# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1a
_database_code_depnum_ccdc_archive 'CCDC 2025175'
loop_
_audit_author_name
_audit_author_address
'Tadashi Hyodo'
;Tokushima Bunri University
Japan
;
_audit_update_record             
;
2020-08-25 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C64 H68 Cl4 N4 O10'
_chemical_formula_weight         1195.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.217(3)
_cell_length_b                   11.2747(18)
_cell_length_c                   16.415(3)
_cell_angle_alpha                90
_cell_angle_beta                 117.459(3)
_cell_angle_gamma                90
_cell_volume                     2827.4(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.404
_exptl_crystal_F_000             1256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.440
_shelx_estimated_absorpt_T_min   0.641
_shelx_estimated_absorpt_T_max   0.792
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7090
_exptl_absorpt_correction_T_max  0.8081
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            35202
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.875
_diffrn_reflns_theta_max         79.085
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5926
_reflns_number_gt                5851
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0544P)²+1.2233P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5926
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0312
_refine_ls_wR_factor_ref         0.0998
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.89275(8) 0.48799(11) 0.51740(8) 0.0140(2) Uani 1 1 d . . . . .
H1A H 0.842324 0.454340 0.463005 0.017 Uiso 1 1 calc R U . . .
H1AB H 0.928028 0.535280 0.495674 0.017 Uiso 1 1 calc R U . . .
C2 C 0.94867(8) 0.38720(11) 0.57887(9) 0.0154(2) Uani 1 1 d . . . . .
H2 H 0.968754 0.335295 0.542853 0.018 Uiso 1 1 calc R U . . .
C3 C 1.02880(8) 0.43915(12) 0.66124(9) 0.0186(3) Uani 1 1 d . . . . .
H3A H 1.065594 0.374353 0.701029 0.022 Uiso 1 1 calc R U . . .
H3AB H 1.064448 0.485842 0.639649 0.022 Uiso 1 1 calc R U . . .
C4 C 0.99713(8) 0.51877(12) 0.71529(8) 0.0164(2) Uani 1 1 d . . . . .
H4 H 1.048813 0.553127 0.769280 0.020 Uiso 1 1 calc R U . . .
C5 C 0.94281(8) 0.44537(11) 0.74890(8) 0.0150(2) Uani 1 1 d . . . . .
H5A H 0.923629 0.496504 0.785282 0.018 Uiso 1 1 calc R U . . .
H5AB H 0.979469 0.380968 0.789356 0.018 Uiso 1 1 calc R U . . .
C6 C 0.86174(7) 0.39116(11) 0.66754(8) 0.0123(2) Uani 1 1 d . . . . .
C7 C 0.89371(8) 0.31339(11) 0.61184(9) 0.0149(2) Uani 1 1 d . . . . .
H7A H 0.929369 0.247049 0.650521 0.018 Uiso 1 1 calc R U . . .
H7AB H 0.842706 0.279366 0.558219 0.018 Uiso 1 1 calc R U . . .
C8 C 0.94016(8) 0.61966(11) 0.65401(8) 0.0153(2) Uani 1 1 d . . . . .
H8A H 0.975095 0.668528 0.632778 0.018 Uiso 1 1 calc R U . . .
H8AB H 0.920638 0.671198 0.689887 0.018 Uiso 1 1 calc R U . . .
C9 C 0.81069(8) 0.32110(11) 0.70683(8) 0.0131(2) Uani 1 1 d . . . . .
C10 C 0.78549(8) 0.37535(11) 0.76793(9) 0.0162(2) Uani 1 1 d . . . . .
H10 H 0.795673 0.457825 0.779948 0.019 Uiso 1 1 calc R U . . .
C11 C 0.74606(8) 0.31168(12) 0.81131(9) 0.0171(3) Uani 1 1 d . . . . .
H11 H 0.730625 0.350185 0.853276 0.021 Uiso 1 1 calc R U . . .
C12 C 0.72938(8) 0.19221(11) 0.79322(8) 0.0147(2) Uani 1 1 d . . . . .
C13 C 0.75084(8) 0.13806(11) 0.73037(8) 0.0150(2) Uani 1 1 d . . . . .
C14 C 0.79160(8) 0.20130(11) 0.68794(8) 0.0141(2) Uani 1 1 d . . . . .
H14 H 0.806499 0.162335 0.645744 0.017 Uiso 1 1 calc R U . . .
C15 C 0.60643(8) 0.10554(11) 0.79587(8) 0.0145(2) Uani 1 1 d . . . . .
C16 C 0.57520(8) -0.00098(11) 0.81470(9) 0.0166(3) Uani 1 1 d . . . . .
H16 H 0.613414 -0.056595 0.858192 0.020 Uiso 1 1 calc R U . . .
C17 C 0.48717(8) -0.02023(11) 0.76723(9) 0.0161(2) Uani 1 1 d . . . . .
H17 H 0.460707 -0.090238 0.775191 0.019 Uiso 1 1 calc R U . . .
C18 C 0.43795(8) 0.06998(11) 0.70574(8) 0.0143(2) Uani 1 1 d . . . . .
C19 C 0.30036(8) 0.14292(11) 0.59924(9) 0.0155(2) Uani 1 1 d . . . . .
C20 C 0.26213(8) 0.22214(11) 0.63405(8) 0.0151(2) Uani 1 1 d . . . . .
C21 C 0.21147(8) 0.31570(11) 0.58097(8) 0.0141(2) Uani 1 1 d . . . . .
H21 H 0.186536 0.370269 0.606402 0.017 Uiso 1 1 calc R U . . .
C22 C 0.19691(7) 0.33012(11) 0.49035(8) 0.0131(2) Uani 1 1 d . . . . .
C23 C 0.23470(9) 0.24709(12) 0.45587(9) 0.0181(3) Uani 1 1 d . . . . .
H23 H 0.224653 0.254046 0.394094 0.022 Uiso 1 1 calc R U . . .
C24 C 0.28650(9) 0.15477(12) 0.50955(9) 0.0193(3) Uani 1 1 d . . . . .
H24 H 0.312205 0.100204 0.484935 0.023 Uiso 1 1 calc R U . . .
C25 C 0.14070(7) 0.43116(11) 0.43005(8) 0.0120(2) Uani 1 1 d . . . . .
C26 C 0.19484(8) 0.50748(10) 0.39556(8) 0.0122(2) Uani 1 1 d . . . . .
H26A H 0.246113 0.541612 0.448836 0.015 Uiso 1 1 calc R U . . .
H26B H 0.216597 0.456611 0.361293 0.015 Uiso 1 1 calc R U . . .
C27 C 0.49947(10) 0.36213(15) 0.92196(11) 0.0305(3) Uani 1 1 d . . . . .
H27A H 0.495897 0.448996 0.912066 0.037 Uiso 1 1 calc R U . . .
H27B H 0.464986 0.323268 0.861756 0.037 Uiso 1 1 calc R U . . .
C28 C 0.59360(10) 0.32292(14) 0.96200(11) 0.0279(3) Uani 1 1 d . . . . .
H28A H 0.616931 0.342596 0.918666 0.034 Uiso 1 1 calc R U . . .
H28B H 0.628747 0.366305 1.019974 0.034 Uiso 1 1 calc R U . . .
C29 C 0.56596(10) 0.16985(14) 1.04024(10) 0.0266(3) Uani 1 1 d . . . . .
H29A H 0.600414 0.209476 1.100132 0.032 Uiso 1 1 calc R U . . .
H29B H 0.569915 0.083117 1.050812 0.032 Uiso 1 1 calc R U . . .
C30 C 0.47166(11) 0.20838(15) 1.00025(12) 0.0314(3) Uani 1 1 d . . . . .
H30A H 0.436481 0.164517 0.942521 0.038 Uiso 1 1 calc R U . . .
H30B H 0.448532 0.189153 1.043838 0.038 Uiso 1 1 calc R U . . .
C31 C 0.97655(10) 0.61687(13) 1.00149(11) 0.0276(3) Uani 1 1 d . . . . .
H31A H 0.935610 0.683577 0.972428 0.033 Uiso 1 1 calc R U . . .
H31B H 1.022480 0.644082 1.061930 0.033 Uiso 1 1 calc R U . . .
C32 C 1.07223(10) 0.48565(15) 0.98501(11) 0.0287(3) Uani 1 1 d . . . . .
H32A H 1.120750 0.509330 1.045002 0.034 Uiso 1 1 calc R U . . .
H32B H 1.097824 0.460915 0.944651 0.034 Uiso 1 1 calc R U . . .
N1 N 0.55743(7) 0.18821(10) 0.74008(8) 0.0163(2) Uani 1 1 d . . . . .
N2 N 0.46934(7) 0.17013(10) 0.69336(8) 0.0163(2) Uani 1 1 d . . . . .
O1 O 0.69519(6) 0.12442(8) 0.84060(6) 0.01768(19) Uani 1 1 d . . . . .
O2 O 0.34986(6) 0.04873(8) 0.65370(6) 0.01806(19) Uani 1 1 d . . . . .
O3 O 0.46365(8) 0.33207(11) 0.98220(9) 0.0379(3) Uani 1 1 d . . . . .
O4 O 0.60164(8) 0.19927(10) 0.97949(8) 0.0310(3) Uani 1 1 d . . . . .
O5 O 1.01583(8) 0.58363(10) 0.94521(7) 0.0295(2) Uani 1 1 d . . . . .
Cl1 Cl 0.72640(2) -0.01041(3) 0.70457(2) 0.02124(9) Uani 1 1 d . . . . .
Cl2 Cl 0.27802(2) 0.20337(3) 0.74578(2) 0.02391(10) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.5299(17) . ?
C1 C25 1.5378(16) 3_666 ?
C1 H1A 0.9900 . ?
C1 H1AB 0.9900 . ?
C2 C7 1.5340(16) . ?
C2 C3 1.5344(18) . ?
C2 H2 1.0000 . ?
C3 C4 1.5285(18) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C5 1.5295(16) . ?
C4 C8 1.5355(17) . ?
C4 H4 1.0000 . ?
C5 C6 1.5448(16) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 C9 1.5283(16) . ?
C6 C7 1.5400(16) . ?
C6 C26 1.5482(16) 3_666 ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C25 1.5488(16) 3_666 ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C14 1.3909(17) . ?
C9 C10 1.4035(17) . ?
C10 C11 1.3888(18) . ?
C10 H10 0.9500 . ?
C11 C12 1.3806(18) . ?
C11 H11 0.9500 . ?
C12 C13 1.3875(18) . ?
C12 O1 1.3992(14) . ?
C13 C14 1.3916(17) . ?
C13 Cl1 1.7303(13) . ?
C14 H14 0.9500 . ?
C15 N1 1.3064(17) . ?
C15 O1 1.3729(15) . ?
C15 C16 1.4072(17) . ?
C16 C17 1.3647(18) . ?
C16 H16 0.9500 . ?
C17 C18 1.4081(17) . ?
C17 H17 0.9500 . ?
C18 N2 1.3076(16) . ?
C18 O2 1.3757(15) . ?
C19 C20 1.3799(18) . ?
C19 C24 1.3850(18) . ?
C19 O2 1.3967(15) . ?
C20 C21 1.3898(18) . ?
C20 Cl2 1.7380(13) . ?
C21 C22 1.3993(17) . ?
C21 H21 0.9500 . ?
C22 C23 1.3999(17) . ?
C22 C25 1.5267(16) . ?
C23 C24 1.3895(18) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.5544(16) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 O3 1.4266(18) . ?
C27 C28 1.507(2) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 O4 1.417(2) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 O4 1.4306(18) . ?
C29 C30 1.508(2) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 O3 1.419(2) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 O5 1.4239(18) . ?
C31 C32 1.504(2) 3_767 ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 O5 1.416(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
N1 N2 1.3628(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C25 110.79(10) . 3_666 ?
C2 C1 H1A 109.5 . . ?
C25 C1 H1A 109.5 3_666 . ?
C2 C1 H1AB 109.5 . . ?
C25 C1 H1AB 109.5 3_666 . ?
H1A C1 H1AB 108.1 . . ?
C1 C2 C7 109.43(10) . . ?
C1 C2 C3 109.53(10) . . ?
C7 C2 C3 110.27(10) . . ?
C1 C2 H2 109.2 . . ?
C7 C2 H2 109.2 . . ?
C3 C2 H2 109.2 . . ?
C4 C3 C2 108.62(10) . . ?
C4 C3 H3A 110.0 . . ?
C2 C3 H3A 110.0 . . ?
C4 C3 H3AB 110.0 . . ?
C2 C3 H3AB 110.0 . . ?
H3A C3 H3AB 108.3 . . ?
C3 C4 C5 109.43(11) . . ?
C3 C4 C8 110.23(10) . . ?
C5 C4 C8 108.96(10) . . ?
C3 C4 H4 109.4 . . ?
C5 C4 H4 109.4 . . ?
C8 C4 H4 109.4 . . ?
C4 C5 C6 111.18(10) . . ?
C4 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
C4 C5 H5AB 109.4 . . ?
C6 C5 H5AB 109.4 . . ?
H5A C5 H5AB 108.0 . . ?
C9 C6 C7 112.88(10) . . ?
C9 C6 C5 107.81(9) . . ?
C7 C6 C5 108.10(10) . . ?
C9 C6 C26 110.91(9) . 3_666 ?
C7 C6 C26 108.06(9) . 3_666 ?
C5 C6 C26 108.98(10) . 3_666 ?
C2 C7 C6 110.37(10) . . ?
C2 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C2 C7 H7AB 109.6 . . ?
C6 C7 H7AB 109.6 . . ?
H7A C7 H7AB 108.1 . . ?
C4 C8 C25 110.48(10) . 3_666 ?
C4 C8 H8A 109.6 . . ?
C25 C8 H8A 109.6 3_666 . ?
C4 C8 H8AB 109.6 . . ?
C25 C8 H8AB 109.6 3_666 . ?
H8A C8 H8AB 108.1 . . ?
C14 C9 C10 117.60(11) . . ?
C14 C9 C6 122.05(11) . . ?
C10 C9 C6 120.26(11) . . ?
C11 C10 C9 121.76(12) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C12 C11 C10 119.76(12) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 119.27(11) . . ?
C11 C12 O1 120.83(11) . . ?
C13 C12 O1 119.83(11) . . ?
C12 C13 C14 121.01(12) . . ?
C12 C13 Cl1 119.31(10) . . ?
C14 C13 Cl1 119.67(10) . . ?
C9 C14 C13 120.52(11) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
N1 C15 O1 117.64(11) . . ?
N1 C15 C16 125.05(12) . . ?
O1 C15 C16 117.30(11) . . ?
C17 C16 C15 116.52(11) . . ?
C17 C16 H16 121.7 . . ?
C15 C16 H16 121.7 . . ?
C16 C17 C18 115.93(11) . . ?
C16 C17 H17 122.0 . . ?
C18 C17 H17 122.0 . . ?
N2 C18 O2 118.05(11) . . ?
N2 C18 C17 125.44(11) . . ?
O2 C18 C17 116.49(11) . . ?
C20 C19 C24 119.76(12) . . ?
C20 C19 O2 119.60(11) . . ?
C24 C19 O2 120.59(11) . . ?
C19 C20 C21 120.86(11) . . ?
C19 C20 Cl2 119.01(10) . . ?
C21 C20 Cl2 120.12(10) . . ?
C20 C21 C22 120.50(11) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C23 117.60(11) . . ?
C21 C22 C25 121.68(11) . . ?
C23 C22 C25 120.71(11) . . ?
C24 C23 C22 121.78(12) . . ?
C24 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
C19 C24 C23 119.47(12) . . ?
C19 C24 H24 120.3 . . ?
C23 C24 H24 120.3 . . ?
C22 C25 C1 111.59(10) . 3_666 ?
C22 C25 C8 110.01(10) . 3_666 ?
C1 C25 C8 107.68(10) 3_666 3_666 ?
C22 C25 C26 109.99(9) . . ?
C1 C25 C26 108.59(10) 3_666 . ?
C8 C25 C26 108.91(9) 3_666 . ?
C6 C26 C25 110.75(9) 3_666 . ?
C6 C26 H26A 109.5 3_666 . ?
C25 C26 H26A 109.5 . . ?
C6 C26 H26B 109.5 3_666 . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
O3 C27 C28 110.46(12) . . ?
O3 C27 H27A 109.6 . . ?
C28 C27 H27A 109.6 . . ?
O3 C27 H27B 109.6 . . ?
C28 C27 H27B 109.6 . . ?
H27A C27 H27B 108.1 . . ?
O4 C28 C27 111.22(13) . . ?
O4 C28 H28A 109.4 . . ?
C27 C28 H28A 109.4 . . ?
O4 C28 H28B 109.4 . . ?
C27 C28 H28B 109.4 . . ?
H28A C28 H28B 108.0 . . ?
O4 C29 C30 110.61(12) . . ?
O4 C29 H29A 109.5 . . ?
C30 C29 H29A 109.5 . . ?
O4 C29 H29B 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 108.1 . . ?
O3 C30 C29 110.82(13) . . ?
O3 C30 H30A 109.5 . . ?
C29 C30 H30A 109.5 . . ?
O3 C30 H30B 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 108.1 . . ?
O5 C31 C32 110.97(12) . 3_767 ?
O5 C31 H31A 109.4 . . ?
C32 C31 H31A 109.4 3_767 . ?
O5 C31 H31B 109.4 . . ?
C32 C31 H31B 109.4 3_767 . ?
H31A C31 H31B 108.0 . . ?
O5 C32 C31 110.90(12) . 3_767 ?
O5 C32 H32A 109.5 . . ?
C31 C32 H32A 109.5 3_767 . ?
O5 C32 H32B 109.5 . . ?
C31 C32 H32B 109.5 3_767 . ?
H32A C32 H32B 108.0 . . ?
C15 N1 N2 118.63(10) . . ?
C18 N2 N1 118.31(10) . . ?
C15 O1 C12 115.93(9) . . ?
C18 O2 C19 115.95(10) . . ?
C30 O3 C27 110.29(12) . . ?
C28 O4 C29 109.64(11) . . ?
C32 O5 C31 109.62(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C25 C1 C2 C7 59.61(13) 3_666 . . . ?
C25 C1 C2 C3 -61.38(12) 3_666 . . . ?
C1 C2 C3 C4 60.15(13) . . . . ?
C7 C2 C3 C4 -60.33(13) . . . . ?
C2 C3 C4 C5 60.08(13) . . . . ?
C2 C3 C4 C8 -59.74(13) . . . . ?
C3 C4 C5 C6 -60.54(13) . . . . ?
C8 C4 C5 C6 60.05(13) . . . . ?
C4 C5 C6 C9 -179.22(10) . . . . ?
C4 C5 C6 C7 58.46(13) . . . . ?
C4 C5 C6 C26 -58.76(13) . . . 3_666 ?
C1 C2 C7 C6 -60.47(13) . . . . ?
C3 C2 C7 C6 60.06(13) . . . . ?
C9 C6 C7 C2 -176.86(10) . . . . ?
C5 C6 C7 C2 -57.69(13) . . . . ?
C26 C6 C7 C2 60.12(12) 3_666 . . . ?
C3 C4 C8 C25 59.92(13) . . . 3_666 ?
C5 C4 C8 C25 -60.19(13) . . . 3_666 ?
C7 C6 C9 C14 -3.80(16) . . . . ?
C5 C6 C9 C14 -123.13(12) . . . . ?
C26 C6 C9 C14 117.62(12) 3_666 . . . ?
C7 C6 C9 C10 172.71(11) . . . . ?
C5 C6 C9 C10 53.38(14) . . . . ?
C26 C6 C9 C10 -65.87(14) 3_666 . . . ?
C14 C9 C10 C11 2.56(18) . . . . ?
C6 C9 C10 C11 -174.11(11) . . . . ?
C9 C10 C11 C12 -1.19(19) . . . . ?
C10 C11 C12 C13 -1.25(19) . . . . ?
C10 C11 C12 O1 175.64(11) . . . . ?
C11 C12 C13 C14 2.29(18) . . . . ?
O1 C12 C13 C14 -174.64(11) . . . . ?
C11 C12 C13 Cl1 -177.71(10) . . . . ?
O1 C12 C13 Cl1 5.37(16) . . . . ?
C10 C9 C14 C13 -1.51(17) . . . . ?
C6 C9 C14 C13 175.09(11) . . . . ?
C12 C13 C14 C9 -0.88(18) . . . . ?
Cl1 C13 C14 C9 179.11(9) . . . . ?
N1 C15 C16 C17 3.1(2) . . . . ?
O1 C15 C16 C17 -177.75(11) . . . . ?
C15 C16 C17 C18 -0.77(18) . . . . ?
C16 C17 C18 N2 -2.34(19) . . . . ?
C16 C17 C18 O2 176.47(11) . . . . ?
C24 C19 C20 C21 -1.58(18) . . . . ?
O2 C19 C20 C21 -179.05(11) . . . . ?
C24 C19 C20 Cl2 178.32(10) . . . . ?
O2 C19 C20 Cl2 0.85(16) . . . . ?
C19 C20 C21 C22 1.17(18) . . . . ?
Cl2 C20 C21 C22 -178.73(9) . . . . ?
C20 C21 C22 C23 0.30(17) . . . . ?
C20 C21 C22 C25 179.29(11) . . . . ?
C21 C22 C23 C24 -1.37(19) . . . . ?
C25 C22 C23 C24 179.63(11) . . . . ?
C20 C19 C24 C23 0.51(19) . . . . ?
O2 C19 C24 C23 177.95(11) . . . . ?
C22 C23 C24 C19 1.0(2) . . . . ?
C21 C22 C25 C1 1.80(15) . . . 3_666 ?
C23 C22 C25 C1 -179.25(11) . . . 3_666 ?
C21 C22 C25 C8 -117.66(12) . . . 3_666 ?
C23 C22 C25 C8 61.30(14) . . . 3_666 ?
C21 C22 C25 C26 122.38(12) . . . . ?
C23 C22 C25 C26 -58.66(14) . . . . ?
C22 C25 C26 C6 178.73(9) . . . 3_666 ?
C1 C25 C26 C6 -58.89(12) 3_666 . . 3_666 ?
C8 C25 C26 C6 58.10(12) 3_666 . . 3_666 ?
O3 C27 C28 O4 57.63(18) . . . . ?
O4 C29 C30 O3 -57.74(18) . . . . ?
O1 C15 N1 N2 178.52(10) . . . . ?
C16 C15 N1 N2 -2.36(19) . . . . ?
O2 C18 N2 N1 -175.57(10) . . . . ?
C17 C18 N2 N1 3.22(19) . . . . ?
C15 N1 N2 C18 -0.81(17) . . . . ?
N1 C15 O1 C12 -31.25(16) . . . . ?
C16 C15 O1 C12 149.56(12) . . . . ?
C11 C12 O1 C15 98.35(14) . . . . ?
C13 C12 O1 C15 -84.78(14) . . . . ?
N2 C18 O2 C19 -6.78(16) . . . . ?
C17 C18 O2 C19 174.32(11) . . . . ?
C20 C19 O2 C18 -91.02(14) . . . . ?
C24 C19 O2 C18 91.53(14) . . . . ?
C29 C30 O3 C27 57.12(18) . . . . ?
C28 C27 O3 C30 -56.74(18) . . . . ?
C27 C28 O4 C29 -57.58(16) . . . . ?
C30 C29 O4 C28 57.39(17) . . . . ?
C31 C32 O5 C31 57.13(17) 3_767 . . . ?
C32 C31 O5 C32 -57.17(17) 3_767 . . . ?

_refine_diff_density_max         0.517
_refine_diff_density_min         -0.593
_refine_diff_density_rms         0.148

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1b
_database_code_depnum_ccdc_archive 'CCDC 2025176'
loop_
_audit_author_name
_audit_author_address
'Tadashi Hyodo'
;Tokushima Bunri University
Japan
;
_audit_update_record             
;
2020-08-25 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C64 H68 Cl4 N4 O7'
_chemical_formula_weight         1147.02

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.1722(16)
_cell_length_b                   11.3008(10)
_cell_length_c                   16.1727(15)
_cell_angle_alpha                90
_cell_angle_beta                 117.160(2)
_cell_angle_gamma                90
_cell_volume                     2792.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.405
_shelx_estimated_absorpt_T_min   0.761
_shelx_estimated_absorpt_T_max   0.795
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7726
_exptl_absorpt_correction_T_max  0.8370
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            36622
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.867
_diffrn_reflns_theta_max         79.705
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             5859
_reflns_number_gt                5721
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1015P)²+1.7574P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5859
_refine_ls_number_parameters     380
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1665
_refine_ls_wR_factor_gt          0.1454
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.161
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C31 C 1.0600(10) 0.5216(16) 0.9961(8) 0.106(6) Uani 0.500(0) 1 d D U P A -1
H31A H 1.122183 0.529906 1.042381 0.127 Uiso 0.500(0) 1 calc R U P A -1
H31B H 1.056323 0.524254 0.933223 0.127 Uiso 0.500(0) 1 calc R U P A -1
C32 C 1.0072(17) 0.6203(16) 1.007(2) 0.199(10) Uani 0.500(0) 1 d D U P A -1
H32A H 0.984237 0.676452 0.954303 0.238 Uiso 0.500(0) 1 calc R U P A -1
H32B H 1.037876 0.663061 1.066906 0.238 Uiso 0.500(0) 1 calc R U P A -1
C33 C 0.9320(5) 0.5234(8) 1.0049(6) 0.048(3) Uani 0.500(0) 1 d . . P A -1
H33A H 0.898138 0.561018 1.033585 0.057 Uiso 0.500(0) 1 calc R U P A -1
H33B H 0.890799 0.505793 0.939349 0.057 Uiso 0.500(0) 1 calc R U P A -1
C34 C 0.9667(3) 0.4169(4) 1.0509(3) 0.0289(9) Uani 0.500(0) 1 d . . P A -1
H34A H 0.998556 0.426151 1.119264 0.035 Uiso 0.500(0) 1 calc R U P A -1
H34B H 0.922080 0.353717 1.034207 0.035 Uiso 0.500(0) 1 calc R U P A -1
O4 O 1.0226(4) 0.4002(4) 1.0107(3) 0.0498(14) Uani 0.500(0) 1 d . . P A -1
C1 C 0.94244(11) 0.44739(16) 0.75273(12) 0.0194(4) Uani 1 1 d . . . . .
H1A H 0.922581 0.497466 0.789704 0.023 Uiso 1 1 calc R U . . .
H1AB H 0.979020 0.382903 0.793319 0.023 Uiso 1 1 calc R U . . .
C2 C 0.99711(11) 0.52196(17) 0.71953(13) 0.0209(4) Uani 1 1 d . . . . .
H2 H 1.048468 0.555803 0.774584 0.025 Uiso 1 1 calc R U . . .
C3 C 1.02965(11) 0.44414(18) 0.66424(13) 0.0230(4) Uani 1 1 d . . . . .
H3A H 1.066361 0.379146 0.703985 0.028 Uiso 1 1 calc R U . . .
H3AB H 1.065594 0.491733 0.643091 0.028 Uiso 1 1 calc R U . . .
C4 C 0.94071(11) 0.62302(16) 0.65820(12) 0.0192(4) Uani 1 1 d . . . . .
H4A H 0.976131 0.672316 0.637403 0.023 Uiso 1 1 calc R U . . .
H4AB H 0.920726 0.673771 0.694697 0.023 Uiso 1 1 calc R U . . .
C5 C 0.86040(11) 0.57340(15) 0.57250(11) 0.0153(3) Uani 1 1 d . . . . .
C6 C 0.80467(11) 0.67499(15) 0.51262(12) 0.0169(3) Uani 1 1 d . . . . .
C7 C 0.76884(13) 0.75903(17) 0.54924(13) 0.0241(4) Uani 1 1 d . . . . .
H7 H 0.780233 0.752607 0.612334 0.029 Uiso 1 1 calc R U . . .
C8 C 0.71709(13) 0.85149(18) 0.49561(14) 0.0258(4) Uani 1 1 d . . . . .
H8 H 0.693257 0.907151 0.521884 0.031 Uiso 1 1 calc R U . . .
C9 C 0.70042(11) 0.86215(16) 0.40382(13) 0.0200(4) Uani 1 1 d . . . . .
C10 C 0.73621(12) 0.78158(16) 0.36695(12) 0.0203(4) Uani 1 1 d . . . . .
C11 C 0.78762(12) 0.68841(15) 0.41999(12) 0.0190(3) Uani 1 1 d . . . . .
H11 H 0.811333 0.633475 0.393078 0.023 Uiso 1 1 calc R U . . .
C12 C 0.56296(11) 0.93715(16) 0.29900(12) 0.0192(4) Uani 1 1 d . . . . .
C13 C 0.51459(12) 1.02467(16) 0.23358(13) 0.0218(4) Uani 1 1 d . . . . .
H13 H 0.541496 1.093008 0.223734 0.026 Uiso 1 1 calc R U . . .
C14 C 0.42695(13) 1.00517(16) 0.18541(14) 0.0224(4) Uani 1 1 d . . . . .
H14 H 0.389236 1.058898 0.139352 0.027 Uiso 1 1 calc R U . . .
C15 C 0.39496(11) 0.90124(16) 0.20731(13) 0.0195(4) Uani 1 1 d . . . . .
C16 C 0.27178(11) 0.81132(16) 0.20703(12) 0.0190(4) Uani 1 1 d . . . . .
C17 C 0.25579(12) 0.69237(17) 0.18705(13) 0.0219(4) Uani 1 1 d . . . . .
H17 H 0.271910 0.655660 0.144261 0.026 Uiso 1 1 calc R U . . .
C18 C 0.21598(12) 0.62660(16) 0.22989(13) 0.0207(4) Uani 1 1 d . . . . .
H18 H 0.206481 0.544396 0.216903 0.025 Uiso 1 1 calc R U . . .
C19 C 0.18941(11) 0.67842(15) 0.29185(12) 0.0171(3) Uani 1 1 d . . . . .
C20 C 0.20775(11) 0.79800(15) 0.31247(12) 0.0185(3) Uani 1 1 d . . . . .
H20 H 0.192104 0.835300 0.355410 0.022 Uiso 1 1 calc R U . . .
C21 C 0.24879(11) 0.86306(16) 0.27063(13) 0.0194(4) Uani 1 1 d . . . . .
C22 C 0.13783(11) 0.60617(15) 0.33031(12) 0.0160(3) Uani 1 1 d . . . . .
C23 C 0.19404(11) 0.50408(14) 0.39329(12) 0.0156(3) Uani 1 1 d . . . . .
H23A H 0.245162 0.537485 0.447562 0.019 Uiso 1 1 calc R U . . .
H23B H 0.216066 0.454202 0.358139 0.019 Uiso 1 1 calc R U . . .
C24 C 0.10496(12) 0.68220(15) 0.38706(13) 0.0191(4) Uani 1 1 d . . . . .
H24A H 0.155585 0.716091 0.441584 0.023 Uiso 1 1 calc R U . . .
H24B H 0.069138 0.748443 0.348271 0.023 Uiso 1 1 calc R U . . .
C25 C 0.04990(11) 0.60706(16) 0.41991(13) 0.0197(4) Uani 1 1 d . . . . .
H25 H 0.029270 0.657802 0.456667 0.024 Uiso 1 1 calc R U . . .
C26 C 0.10573(11) 0.50626(15) 0.48119(12) 0.0177(3) Uani 1 1 d . . . . .
H26A H 0.070374 0.458440 0.502983 0.021 Uiso 1 1 calc R U . . .
H26B H 0.155989 0.539506 0.536418 0.021 Uiso 1 1 calc R U . . .
C27 C 0.42440(17) 0.8529(3) -0.03570(19) 0.0453(6) Uani 1 1 d . . . . .
H27A H 0.430336 0.940069 -0.030083 0.054 Uiso 1 1 calc R U . . .
H27B H 0.392703 0.832054 -0.102424 0.054 Uiso 1 1 calc R U . . .
C28 C 0.5131(2) 0.7951(3) 0.0086(2) 0.0541(7) Uani 1 1 d . . . . .
H28A H 0.553879 0.836657 0.066052 0.065 Uiso 1 1 calc R U . . .
H28B H 0.539163 0.791125 -0.034788 0.065 Uiso 1 1 calc R U . . .
C29 C 0.4897(3) 0.6741(4) 0.0292(4) 0.0884(13) Uani 1 1 d . . . . .
H29A H 0.537717 0.641186 0.086563 0.106 Uiso 1 1 calc R U . . .
H29B H 0.477459 0.619058 -0.022913 0.106 Uiso 1 1 calc R U . . .
C30 C 0.4080(2) 0.6942(3) 0.0417(2) 0.0534(7) Uani 1 1 d . . . . .
H30A H 0.362069 0.636445 0.004090 0.064 Uiso 1 1 calc R U . . .
H30B H 0.421780 0.684040 0.107720 0.064 Uiso 1 1 calc R U . . .
N1 N 0.53091(10) 0.84028(14) 0.31536(12) 0.0231(3) Uani 1 1 d . . . . .
N2 N 0.44291(10) 0.82190(14) 0.26784(12) 0.0231(3) Uani 1 1 d . . . . .
O1 O 0.65126(8) 0.95686(12) 0.34984(10) 0.0231(3) Uani 1 1 d . . . . .
O2 O 0.30667(8) 0.88159(12) 0.16088(9) 0.0221(3) Uani 1 1 d . . . . .
O3 O 0.37856(14) 0.81002(18) 0.01236(14) 0.0479(5) Uani 1 1 d . . . . .
Cl1 Cl 0.71666(4) 0.79865(4) 0.25227(3) 0.03605(18) Uani 1 1 d . . . . .
Cl2 Cl 0.27163(3) 1.01150(4) 0.29701(3) 0.02746(16) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C31 C32 1.498(17) . ?
C31 O4 1.577(15) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.68(2) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.397(10) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 O4 1.397(7) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C1 C2 1.530(2) . ?
C1 C22 1.543(2) 3_666 ?
C1 H1A 0.9900 . ?
C1 H1AB 0.9900 . ?
C2 C3 1.530(3) . ?
C2 C4 1.533(2) . ?
C2 H2 1.0000 . ?
C3 C25 1.535(3) 3_666 ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C5 1.547(2) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C6 1.525(2) . ?
C5 C26 1.537(2) 3_666 ?
C5 C23 1.555(2) 3_666 ?
C6 C11 1.397(2) . ?
C6 C7 1.401(3) . ?
C7 C8 1.389(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.377(3) . ?
C9 O1 1.395(2) . ?
C10 C11 1.390(3) . ?
C10 Cl1 1.7382(18) . ?
C11 H11 0.9500 . ?
C12 N1 1.306(2) . ?
C12 O1 1.374(2) . ?
C12 C13 1.409(2) . ?
C13 C14 1.360(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.409(2) . ?
C14 H14 0.9500 . ?
C15 N2 1.305(2) . ?
C15 O2 1.368(2) . ?
C16 C17 1.380(3) . ?
C16 C21 1.388(3) . ?
C16 O2 1.398(2) . ?
C17 C18 1.390(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.405(2) . ?
C18 H18 0.9500 . ?
C19 C20 1.393(2) . ?
C19 C22 1.530(2) . ?
C20 C21 1.389(2) . ?
C20 H20 0.9500 . ?
C21 Cl2 1.7312(18) . ?
C22 C24 1.540(2) . ?
C22 C23 1.550(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.535(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.527(2) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 O3 1.420(3) . ?
C27 C28 1.505(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.505(6) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.523(6) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 O3 1.405(4) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
N1 N2 1.363(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C32 C31 O4 108.7(11) . . ?
C32 C31 H31A 110.0 . . ?
O4 C31 H31A 110.0 . . ?
C32 C31 H31B 110.0 . . ?
O4 C31 H31B 110.0 . . ?
H31A C31 H31B 108.3 . . ?
C31 C32 C33 90.7(11) . . ?
C31 C32 H32A 113.5 . . ?
C33 C32 H32A 113.5 . . ?
C31 C32 H32B 113.5 . . ?
C33 C32 H32B 113.5 . . ?
H32A C32 H32B 110.8 . . ?
C34 C33 C32 114.4(9) . . ?
C34 C33 H33A 108.7 . . ?
C32 C33 H33A 108.7 . . ?
C34 C33 H33B 108.7 . . ?
C32 C33 H33B 108.7 . . ?
H33A C33 H33B 107.6 . . ?
O4 C34 C33 94.9(6) . . ?
O4 C34 H34A 112.8 . . ?
C33 C34 H34A 112.8 . . ?
O4 C34 H34B 112.8 . . ?
C33 C34 H34B 112.8 . . ?
H34A C34 H34B 110.2 . . ?
C34 O4 C31 111.5(6) . . ?
C2 C1 C22 110.99(14) . 3_666 ?
C2 C1 H1A 109.4 . . ?
C22 C1 H1A 109.4 3_666 . ?
C2 C1 H1AB 109.4 . . ?
C22 C1 H1AB 109.4 3_666 . ?
H1A C1 H1AB 108.0 . . ?
C1 C2 C3 109.56(15) . . ?
C1 C2 C4 109.26(14) . . ?
C3 C2 C4 109.97(15) . . ?
C1 C2 H2 109.3 . . ?
C3 C2 H2 109.3 . . ?
C4 C2 H2 109.3 . . ?
C2 C3 C25 108.68(14) . 3_666 ?
C2 C3 H3A 110.0 . . ?
C25 C3 H3A 110.0 3_666 . ?
C2 C3 H3AB 110.0 . . ?
C25 C3 H3AB 110.0 3_666 . ?
H3A C3 H3AB 108.3 . . ?
C2 C4 C5 110.57(14) . . ?
C2 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C2 C4 H4AB 109.5 . . ?
C5 C4 H4AB 109.5 . . ?
H4A C4 H4AB 108.1 . . ?
C6 C5 C26 111.82(14) . 3_666 ?
C6 C5 C4 109.91(14) . . ?
C26 C5 C4 107.82(14) 3_666 . ?
C6 C5 C23 110.16(13) . 3_666 ?
C26 C5 C23 108.37(13) 3_666 3_666 ?
C4 C5 C23 108.68(13) . 3_666 ?
C11 C6 C7 117.52(16) . . ?
C11 C6 C5 121.74(15) . . ?
C7 C6 C5 120.74(15) . . ?
C8 C7 C6 121.66(17) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C9 C8 C7 119.72(17) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C10 C9 C8 119.51(17) . . ?
C10 C9 O1 119.89(16) . . ?
C8 C9 O1 120.54(17) . . ?
C9 C10 C11 121.12(16) . . ?
C9 C10 Cl1 118.79(14) . . ?
C11 C10 Cl1 120.09(14) . . ?
C10 C11 C6 120.46(17) . . ?
C10 C11 H11 119.8 . . ?
C6 C11 H11 119.8 . . ?
N1 C12 O1 117.84(16) . . ?
N1 C12 C13 125.60(17) . . ?
O1 C12 C13 116.55(16) . . ?
C14 C13 C12 115.80(16) . . ?
C14 C13 H13 122.1 . . ?
C12 C13 H13 122.1 . . ?
C13 C14 C15 116.59(16) . . ?
C13 C14 H14 121.7 . . ?
C15 C14 H14 121.7 . . ?
N2 C15 O2 117.49(16) . . ?
N2 C15 C14 125.19(17) . . ?
O2 C15 C14 117.32(16) . . ?
C17 C16 C21 119.35(16) . . ?
C17 C16 O2 121.07(17) . . ?
C21 C16 O2 119.50(16) . . ?
C16 C17 C18 119.64(17) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 H17 120.2 . . ?
C17 C18 C19 121.77(17) . . ?
C17 C18 H18 119.1 . . ?
C19 C18 H18 119.1 . . ?
C20 C19 C18 117.62(16) . . ?
C20 C19 C22 122.01(15) . . ?
C18 C19 C22 120.29(16) . . ?
C21 C20 C19 120.42(17) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C16 C21 C20 121.14(17) . . ?
C16 C21 Cl2 118.80(14) . . ?
C20 C21 Cl2 120.06(14) . . ?
C19 C22 C24 112.46(14) . . ?
C19 C22 C1 107.97(14) . 3_666 ?
C24 C22 C1 108.22(14) . 3_666 ?
C19 C22 C23 111.22(14) . . ?
C24 C22 C23 108.14(14) . . ?
C1 C22 C23 108.72(14) 3_666 . ?
C22 C23 C5 110.95(13) . 3_666 ?
C22 C23 H23A 109.4 . . ?
C5 C23 H23A 109.4 3_666 . ?
C22 C23 H23B 109.4 . . ?
C5 C23 H23B 109.4 3_666 . ?
H23A C23 H23B 108.0 . . ?
C25 C24 C22 110.42(14) . . ?
C25 C24 H24A 109.6 . . ?
C22 C24 H24A 109.6 . . ?
C25 C24 H24B 109.6 . . ?
C22 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
C26 C25 C3 109.59(15) . 3_666 ?
C26 C25 C24 109.51(14) . . ?
C3 C25 C24 109.94(15) 3_666 . ?
C26 C25 H25 109.3 . . ?
C3 C25 H25 109.3 3_666 . ?
C24 C25 H25 109.3 . . ?
C25 C26 C5 110.95(14) . 3_666 ?
C25 C26 H26A 109.4 . . ?
C5 C26 H26A 109.4 3_666 . ?
C25 C26 H26B 109.4 . . ?
C5 C26 H26B 109.4 3_666 . ?
H26A C26 H26B 108.0 . . ?
O3 C27 C28 106.6(2) . . ?
O3 C27 H27A 110.4 . . ?
C28 C27 H27A 110.4 . . ?
O3 C27 H27B 110.4 . . ?
C28 C27 H27B 110.4 . . ?
H27A C27 H27B 108.6 . . ?
C27 C28 C29 100.6(3) . . ?
C27 C28 H28A 111.6 . . ?
C29 C28 H28A 111.6 . . ?
C27 C28 H28B 111.6 . . ?
C29 C28 H28B 111.6 . . ?
H28A C28 H28B 109.4 . . ?
C28 C29 C30 104.4(3) . . ?
C28 C29 H29A 110.9 . . ?
C30 C29 H29A 110.9 . . ?
C28 C29 H29B 110.9 . . ?
C30 C29 H29B 110.9 . . ?
H29A C29 H29B 108.9 . . ?
O3 C30 C29 107.8(3) . . ?
O3 C30 H30A 110.1 . . ?
C29 C30 H30A 110.1 . . ?
O3 C30 H30B 110.1 . . ?
C29 C30 H30B 110.1 . . ?
H30A C30 H30B 108.5 . . ?
C12 N1 N2 118.37(15) . . ?
C15 N2 N1 118.40(15) . . ?
C12 O1 C9 115.94(14) . . ?
C15 O2 C16 115.89(13) . . ?
C30 O3 C27 107.4(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C31 C32 C33 -11.4(17) . . . . ?
C31 C32 C33 C34 38.0(19) . . . . ?
C32 C33 C34 O4 -46.7(13) . . . . ?
C33 C34 O4 C31 35.3(6) . . . . ?
C32 C31 O4 C34 -14.2(16) . . . . ?
C22 C1 C2 C3 -60.40(19) 3_666 . . . ?
C22 C1 C2 C4 60.14(19) 3_666 . . . ?
C1 C2 C3 C25 60.18(19) . . . 3_666 ?
C4 C2 C3 C25 -59.94(18) . . . 3_666 ?
C1 C2 C4 C5 -60.14(19) . . . . ?
C3 C2 C4 C5 60.15(18) . . . . ?
C2 C4 C5 C6 179.59(14) . . . . ?
C2 C4 C5 C26 -58.29(18) . . . 3_666 ?
C2 C4 C5 C23 58.97(18) . . . 3_666 ?
C26 C5 C6 C11 0.9(2) 3_666 . . . ?
C4 C5 C6 C11 120.59(17) . . . . ?
C23 C5 C6 C11 -119.69(17) 3_666 . . . ?
C26 C5 C6 C7 -178.84(16) 3_666 . . . ?
C4 C5 C6 C7 -59.1(2) . . . . ?
C23 C5 C6 C7 60.6(2) 3_666 . . . ?
C11 C6 C7 C8 1.0(3) . . . . ?
C5 C6 C7 C8 -179.27(17) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
C7 C8 C9 C10 -0.7(3) . . . . ?
C7 C8 C9 O1 -177.65(17) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
O1 C9 C10 C11 178.07(16) . . . . ?
C8 C9 C10 Cl1 -178.44(15) . . . . ?
O1 C9 C10 Cl1 -1.5(2) . . . . ?
C9 C10 C11 C6 -0.5(3) . . . . ?
Cl1 C10 C11 C6 179.10(13) . . . . ?
C7 C6 C11 C10 -0.6(3) . . . . ?
C5 C6 C11 C10 179.68(16) . . . . ?
N1 C12 C13 C14 1.1(3) . . . . ?
O1 C12 C13 C14 -178.48(17) . . . . ?
C12 C13 C14 C15 0.8(3) . . . . ?
C13 C14 C15 N2 -1.9(3) . . . . ?
C13 C14 C15 O2 178.63(17) . . . . ?
C21 C16 C17 C18 0.8(3) . . . . ?
O2 C16 C17 C18 -175.96(16) . . . . ?
C16 C17 C18 C19 1.5(3) . . . . ?
C17 C18 C19 C20 -2.7(3) . . . . ?
C17 C18 C19 C22 174.00(16) . . . . ?
C18 C19 C20 C21 1.7(3) . . . . ?
C22 C19 C20 C21 -174.98(16) . . . . ?
C17 C16 C21 C20 -1.8(3) . . . . ?
O2 C16 C21 C20 174.98(16) . . . . ?
C17 C16 C21 Cl2 178.48(14) . . . . ?
O2 C16 C21 Cl2 -4.7(2) . . . . ?
C19 C20 C21 C16 0.5(3) . . . . ?
C19 C20 C21 Cl2 -179.78(13) . . . . ?
C20 C19 C22 C24 3.7(2) . . . . ?
C18 C19 C22 C24 -172.87(15) . . . . ?
C20 C19 C22 C1 123.05(17) . . . 3_666 ?
C18 C19 C22 C1 -53.5(2) . . . 3_666 ?
C20 C19 C22 C23 -117.74(17) . . . . ?
C18 C19 C22 C23 65.7(2) . . . . ?
C19 C22 C23 C5 -176.71(13) . . . 3_666 ?
C24 C22 C23 C5 59.34(17) . . . 3_666 ?
C1 C22 C23 C5 -57.95(17) 3_666 . . 3_666 ?
C19 C22 C24 C25 177.19(14) . . . . ?
C1 C22 C24 C25 58.01(18) 3_666 . . . ?
C23 C22 C24 C25 -59.61(18) . . . . ?
C22 C24 C25 C26 60.26(19) . . . . ?
C22 C24 C25 C3 -60.20(19) . . . 3_666 ?
C3 C25 C26 C5 60.86(18) 3_666 . . 3_666 ?
C24 C25 C26 C5 -59.82(18) . . . 3_666 ?
O3 C27 C28 C29 36.7(3) . . . . ?
C27 C28 C29 C30 -27.8(4) . . . . ?
C28 C29 C30 O3 10.8(5) . . . . ?
O1 C12 N1 N2 177.56(16) . . . . ?
C13 C12 N1 N2 -2.0(3) . . . . ?
O2 C15 N2 N1 -179.49(16) . . . . ?
C14 C15 N2 N1 1.0(3) . . . . ?
C12 N1 N2 C15 0.9(3) . . . . ?
N1 C12 O1 C9 9.8(2) . . . . ?
C13 C12 O1 C9 -170.56(16) . . . . ?
C10 C9 O1 C12 90.3(2) . . . . ?
C8 C9 O1 C12 -92.8(2) . . . . ?
N2 C15 O2 C16 26.4(2) . . . . ?
C14 C15 O2 C16 -154.05(17) . . . . ?
C17 C16 O2 C15 -98.5(2) . . . . ?
C21 C16 O2 C15 84.8(2) . . . . ?
C29 C30 O3 C27 12.5(4) . . . . ?
C28 C27 O3 C30 -31.5(3) . . . . ?

_refine_diff_density_max         0.835
_refine_diff_density_min         -0.829
_refine_diff_density_rms         0.202

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1c
_database_code_depnum_ccdc_archive 'CCDC 2025177'
loop_
_audit_author_name
_audit_author_address
'Tadashi Hyodo'
;Tokushima Bunri University
Japan
;
_audit_update_record             
;
2020-08-25 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C60 H54 Cl4 N4 O4'
_chemical_formula_weight         1036.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.5240(14)
_cell_length_b                   13.9309(12)
_cell_length_c                   11.3445(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.390(3)
_cell_angle_gamma                90
_cell_volume                     2492.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_F_000             1084
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.592
_shelx_estimated_absorpt_T_min   0.746
_shelx_estimated_absorpt_T_max   0.782
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7244
_exptl_absorpt_correction_T_max  0.8199
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            28692
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.234
_diffrn_reflns_theta_max         79.038
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5228
_reflns_number_gt                4926
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0878P)²+3.0850P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5228
_refine_ls_number_parameters     336
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0643
_refine_ls_wR_factor_ref         0.1824
_refine_ls_wR_factor_gt          0.1706
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.93141(16) 0.58395(17) 0.8604(2) 0.0326(5) Uani 1 1 d . . . . .
H1A H 0.957387 0.632913 0.923597 0.039 Uiso 1 1 calc R U . . .
H1AB H 0.911692 0.530167 0.901797 0.039 Uiso 1 1 calc R U . . .
C2 C 0.99758(16) 0.54732(18) 0.8017(2) 0.0339(5) Uani 1 1 d . . . . .
H2 H 1.045944 0.518260 0.867266 0.041 Uiso 1 1 calc R U . . .
C3 C 1.03055(17) 0.6300(2) 0.7406(2) 0.0392(6) Uani 1 1 d . . . . .
H3A H 1.057898 0.678860 0.803293 0.047 Uiso 1 1 calc R U . . .
H3AB H 1.073257 0.605982 0.702491 0.047 Uiso 1 1 calc R U . . .
C4 C 0.95622(16) 0.67475(18) 0.6420(2) 0.0348(5) Uani 1 1 d . . . . .
H4 H 0.977320 0.729522 0.602385 0.042 Uiso 1 1 calc R U . . .
C5 C 0.91651(15) 0.59893(17) 0.5437(2) 0.0297(5) Uani 1 1 d . . . . .
H5A H 0.959571 0.575815 0.505628 0.036 Uiso 1 1 calc R U . . .
H5AB H 0.869427 0.628125 0.477936 0.036 Uiso 1 1 calc R U . . .
C6 C 0.88262(14) 0.51346(15) 0.60163(19) 0.0254(4) Uani 1 1 d . . . . .
C7 C 0.95715(15) 0.47031(17) 0.7048(2) 0.0299(5) Uani 1 1 d . . . . .
H7A H 0.936362 0.416533 0.744943 0.036 Uiso 1 1 calc R U . . .
H7AB H 1.000307 0.444745 0.668532 0.036 Uiso 1 1 calc R U . . .
C8 C 0.84040(14) 0.44031(16) 0.50184(19) 0.0256(4) Uani 1 1 d . . . . .
C9 C 0.7801(2) 0.4693(2) 0.3945(3) 0.0531(8) Uani 1 1 d . . . . .
H9 H 0.765519 0.535419 0.383841 0.064 Uiso 1 1 calc R U . . .
C10 C 0.7403(2) 0.4054(2) 0.3024(3) 0.0587(9) Uani 1 1 d . . . . .
H10 H 0.699322 0.428243 0.229933 0.070 Uiso 1 1 calc R U . . .
C11 C 0.75910(14) 0.30933(17) 0.3141(2) 0.0292(5) Uani 1 1 d . . . . .
C12 C 0.81662(17) 0.27952(18) 0.4201(2) 0.0365(6) Uani 1 1 d . . . . .
C13 C 0.85712(17) 0.34365(17) 0.5133(2) 0.0367(6) Uani 1 1 d . . . . .
H13 H 0.897117 0.320040 0.586197 0.044 Uiso 1 1 calc R U . . .
C14 C 0.63926(15) 0.24856(17) 0.1621(2) 0.0292(5) Uani 1 1 d . . . . .
C15 C 0.61073(16) 0.22892(17) 0.0347(2) 0.0310(5) Uani 1 1 d . . . . .
H15 H 0.648997 0.214705 -0.010957 0.037 Uiso 1 1 calc R U . . .
C16 C 0.52584(16) 0.23139(18) -0.0194(2) 0.0315(5) Uani 1 1 d . . . . .
H16 H 0.501280 0.219701 -0.105214 0.038 Uiso 1 1 calc R U . . .
C17 C 0.47604(15) 0.25219(17) 0.05829(19) 0.0290(5) Uani 1 1 d . . . . .
C18 C 0.33729(15) 0.28286(19) 0.0716(2) 0.0335(5) Uani 1 1 d . . . . .
C19 C 0.3005(2) 0.3713(2) 0.0488(2) 0.0449(7) Uani 1 1 d . . . . .
C20 C 0.2395(2) 0.39978(19) 0.1027(3) 0.0444(7) Uani 1 1 d . . . . .
H20 H 0.215091 0.461901 0.085510 0.053 Uiso 1 1 calc R U . . .
C21 C 0.21315(15) 0.33898(16) 0.1818(2) 0.0285(5) Uani 1 1 d . . . . .
C22 C 0.25387(15) 0.25076(17) 0.2076(2) 0.0297(5) Uani 1 1 d . . . . .
H22 H 0.239369 0.208343 0.263659 0.036 Uiso 1 1 calc R U . . .
C23 C 0.31530(15) 0.22305(19) 0.1533(2) 0.0335(5) Uani 1 1 d . . . . .
H23 H 0.342232 0.162373 0.172769 0.040 Uiso 1 1 calc R U . . .
C24 C 0.14511(15) 0.37164(15) 0.23870(19) 0.0274(5) Uani 1 1 d . . . . .
C25 C 0.18373(14) 0.44853(15) 0.33862(19) 0.0249(4) Uani 1 1 d . . . . .
H25A H 0.231969 0.420224 0.403334 0.030 Uiso 1 1 calc R U . . .
H25B H 0.205651 0.502645 0.300510 0.030 Uiso 1 1 calc R U . . .
C26 C 0.11149(17) 0.28846(16) 0.3014(2) 0.0327(5) Uani 1 1 d . . . . .
H26A H 0.086789 0.238015 0.239689 0.039 Uiso 1 1 calc R U . . .
H26B H 0.158993 0.259724 0.366947 0.039 Uiso 1 1 calc R U . . .
C27 C 0.4266(2) 0.0079(2) -0.0974(3) 0.0568(8) Uani 1 1 d . . . . .
H27 H 0.375563 0.013588 -0.163609 0.068 Uiso 1 1 calc R U . . .
C28 C 0.4244(2) 0.0154(2) 0.0228(3) 0.0568(8) Uani 1 1 d . . . . .
H28 H 0.371424 0.026075 0.037535 0.068 Uiso 1 1 calc R U . . .
C29 C 0.4969(2) 0.0080(2) 0.1228(3) 0.0565(8) Uani 1 1 d . . . . .
C30 C 0.4943(3) 0.0171(3) 0.2537(4) 0.0654(10) Uani 1 1 d . . . . .
H30A H 0.507216 0.083409 0.281819 0.098 Uiso 1 1 calc R U . . .
H30B H 0.536327 -0.026172 0.306938 0.098 Uiso 1 1 calc R U . . .
H30C H 0.437608 -0.000046 0.257518 0.098 Uiso 1 1 calc R U . . .
N1 N 0.59065(13) 0.26872(15) 0.23048(16) 0.0311(4) Uani 1 1 d . . . . .
N2 N 0.50520(13) 0.27078(15) 0.17633(16) 0.0298(4) Uani 1 1 d . . . . .
O1 O 0.72551(11) 0.24464(13) 0.21898(15) 0.0368(4) Uani 1 1 d . . . . .
O2 O 0.39027(12) 0.25310(15) 0.00336(15) 0.0401(4) Uani 1 1 d . . . . .
Cl2 Cl 0.33073(9) 0.44779(6) -0.05007(10) 0.0840(4) Uani 1 1 d . . . . .
Cl1 Cl 0.84984(10) 0.15989(7) 0.42900(14) 0.0466(5) Uani 0.733(6) 1 d . . P A 1
Cl3 Cl 0.7999(6) 0.1591(2) 0.4670(5) 0.089(4) Uani 0.267(6) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.527(4) . ?
C1 C24 1.548(3) 3_666 ?
C1 H1A 0.9900 . ?
C1 H1AB 0.9900 . ?
C2 C3 1.527(4) . ?
C2 C7 1.539(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.525(4) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C5 1.534(3) . ?
C4 C26 1.534(3) 3_666 ?
C4 H4 1.0000 . ?
C5 C6 1.544(3) . ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 C8 1.528(3) . ?
C6 C25 1.545(3) 3_666 ?
C6 C7 1.545(3) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C13 1.373(3) . ?
C8 C9 1.384(3) . ?
C9 C10 1.381(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.371(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.356(3) . ?
C11 O1 1.388(3) . ?
C12 C13 1.393(3) . ?
C12 Cl1 1.748(3) . ?
C12 Cl3 1.807(5) . ?
C13 H13 0.9500 . ?
C14 N1 1.303(3) . ?
C14 O1 1.379(3) . ?
C14 C15 1.407(3) . ?
C15 C16 1.353(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.404(3) . ?
C16 H16 0.9500 . ?
C17 N2 1.306(3) . ?
C17 O2 1.367(3) . ?
C18 C19 1.364(4) . ?
C18 C23 1.373(4) . ?
C18 O2 1.394(3) . ?
C19 C20 1.385(4) . ?
C19 Cl2 1.725(3) . ?
C20 C21 1.395(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.390(3) . ?
C21 C24 1.524(3) . ?
C22 C23 1.390(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 C26 1.547(3) . ?
C24 C25 1.552(3) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.380(5) . ?
C27 C29 1.396(5) 3_655 ?
C27 H27 0.9500 . ?
C28 C29 1.386(5) . ?
C28 H28 0.9500 . ?
C29 C30 1.503(5) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
N1 N2 1.361(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C24 110.69(18) . 3_666 ?
C2 C1 H1A 109.5 . . ?
C24 C1 H1A 109.5 3_666 . ?
C2 C1 H1AB 109.5 . . ?
C24 C1 H1AB 109.5 3_666 . ?
H1A C1 H1AB 108.1 . . ?
C3 C2 C1 110.2(2) . . ?
C3 C2 C7 109.8(2) . . ?
C1 C2 C7 109.3(2) . . ?
C3 C2 H2 109.2 . . ?
C1 C2 H2 109.2 . . ?
C7 C2 H2 109.2 . . ?
C4 C3 C2 108.8(2) . . ?
C4 C3 H3A 109.9 . . ?
C2 C3 H3A 109.9 . . ?
C4 C3 H3AB 109.9 . . ?
C2 C3 H3AB 109.9 . . ?
H3A C3 H3AB 108.3 . . ?
C3 C4 C5 109.1(2) . . ?
C3 C4 C26 111.0(2) . 3_666 ?
C5 C4 C26 109.1(2) . 3_666 ?
C3 C4 H4 109.2 . . ?
C5 C4 H4 109.2 . . ?
C26 C4 H4 109.2 3_666 . ?
C4 C5 C6 110.61(18) . . ?
C4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
C4 C5 H5AB 109.5 . . ?
C6 C5 H5AB 109.5 . . ?
H5A C5 H5AB 108.1 . . ?
C8 C6 C5 110.02(18) . . ?
C8 C6 C25 109.09(18) . 3_666 ?
C5 C6 C25 108.53(17) . 3_666 ?
C8 C6 C7 112.70(18) . . ?
C5 C6 C7 108.31(18) . . ?
C25 C6 C7 108.10(17) 3_666 . ?
C2 C7 C6 110.35(19) . . ?
C2 C7 H7A 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C2 C7 H7AB 109.6 . . ?
C6 C7 H7AB 109.6 . . ?
H7A C7 H7AB 108.1 . . ?
C13 C8 C9 116.2(2) . . ?
C13 C8 C6 123.3(2) . . ?
C9 C8 C6 120.4(2) . . ?
C10 C9 C8 122.2(2) . . ?
C10 C9 H9 118.9 . . ?
C8 C9 H9 118.9 . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 117.6(2) . . ?
C12 C11 O1 120.1(2) . . ?
C10 C11 O1 122.1(2) . . ?
C11 C12 C13 121.8(2) . . ?
C11 C12 Cl1 117.87(19) . . ?
C13 C12 Cl1 119.77(19) . . ?
C11 C12 Cl3 114.6(2) . . ?
C13 C12 Cl3 117.0(2) . . ?
C8 C13 C12 121.3(2) . . ?
C8 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
N1 C14 O1 117.71(19) . . ?
N1 C14 C15 125.2(2) . . ?
O1 C14 C15 117.1(2) . . ?
C16 C15 C14 116.4(2) . . ?
C16 C15 H15 121.8 . . ?
C14 C15 H15 121.8 . . ?
C15 C16 C17 116.3(2) . . ?
C15 C16 H16 121.8 . . ?
C17 C16 H16 121.8 . . ?
N2 C17 O2 118.7(2) . . ?
N2 C17 C16 125.3(2) . . ?
O2 C17 C16 115.97(19) . . ?
C19 C18 C23 118.9(2) . . ?
C19 C18 O2 118.8(2) . . ?
C23 C18 O2 122.1(2) . . ?
C18 C19 C20 121.1(2) . . ?
C18 C19 Cl2 118.8(2) . . ?
C20 C19 Cl2 120.0(2) . . ?
C19 C20 C21 121.3(2) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C22 C21 C20 116.6(2) . . ?
C22 C21 C24 123.2(2) . . ?
C20 C21 C24 120.2(2) . . ?
C21 C22 C23 121.6(2) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
C18 C23 C22 120.4(2) . . ?
C18 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C21 C24 C26 112.53(18) . . ?
C21 C24 C1 110.97(18) . 3_666 ?
C26 C24 C1 107.8(2) . 3_666 ?
C21 C24 C25 108.74(18) . . ?
C26 C24 C25 107.87(17) . . ?
C1 C24 C25 108.84(17) 3_666 . ?
C6 C25 C24 111.50(18) 3_666 . ?
C6 C25 H25A 109.3 3_666 . ?
C24 C25 H25A 109.3 . . ?
C6 C25 H25B 109.3 3_666 . ?
C24 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?
C4 C26 C24 110.42(19) 3_666 . ?
C4 C26 H26A 109.6 3_666 . ?
C24 C26 H26A 109.6 . . ?
C4 C26 H26B 109.6 3_666 . ?
C24 C26 H26B 109.6 . . ?
H26A C26 H26B 108.1 . . ?
C28 C27 C29 120.6(4) . 3_655 ?
C28 C27 H27 119.7 . . ?
C29 C27 H27 119.7 3_655 . ?
C27 C28 C29 122.1(3) . . ?
C27 C28 H28 118.9 . . ?
C29 C28 H28 118.9 . . ?
C28 C29 C27 117.2(3) . 3_655 ?
C28 C29 C30 122.0(3) . . ?
C27 C29 C30 120.8(4) 3_655 . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C14 N1 N2 118.47(18) . . ?
C17 N2 N1 118.26(19) . . ?
C14 O1 C11 117.08(18) . . ?
C17 O2 C18 119.16(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C24 C1 C2 C3 60.8(2) 3_666 . . . ?
C24 C1 C2 C7 -59.9(2) 3_666 . . . ?
C1 C2 C3 C4 -59.4(3) . . . . ?
C7 C2 C3 C4 61.0(3) . . . . ?
C2 C3 C4 C5 -61.4(3) . . . . ?
C2 C3 C4 C26 58.9(3) . . . 3_666 ?
C3 C4 C5 C6 61.1(3) . . . . ?
C26 C4 C5 C6 -60.3(2) 3_666 . . . ?
C4 C5 C6 C8 177.94(18) . . . . ?
C4 C5 C6 C25 58.7(2) . . . 3_666 ?
C4 C5 C6 C7 -58.5(2) . . . . ?
C3 C2 C7 C6 -59.8(3) . . . . ?
C1 C2 C7 C6 61.1(3) . . . . ?
C8 C6 C7 C2 179.48(19) . . . . ?
C5 C6 C7 C2 57.5(2) . . . . ?
C25 C6 C7 C2 -59.9(2) 3_666 . . . ?
C5 C6 C8 C13 131.5(2) . . . . ?
C25 C6 C8 C13 -109.6(3) 3_666 . . . ?
C7 C6 C8 C13 10.5(3) . . . . ?
C5 C6 C8 C9 -50.5(3) . . . . ?
C25 C6 C8 C9 68.5(3) 3_666 . . . ?
C7 C6 C8 C9 -171.4(3) . . . . ?
C13 C8 C9 C10 -1.6(5) . . . . ?
C6 C8 C9 C10 -179.8(3) . . . . ?
C8 C9 C10 C11 0.2(6) . . . . ?
C9 C10 C11 C12 1.4(5) . . . . ?
C9 C10 C11 O1 -174.5(3) . . . . ?
C10 C11 C12 C13 -1.5(4) . . . . ?
O1 C11 C12 C13 174.4(2) . . . . ?
C10 C11 C12 Cl1 -173.0(3) . . . . ?
O1 C11 C12 Cl1 3.0(4) . . . . ?
C10 C11 C12 Cl3 149.1(5) . . . . ?
O1 C11 C12 Cl3 -34.9(5) . . . . ?
C9 C8 C13 C12 1.4(4) . . . . ?
C6 C8 C13 C12 179.6(2) . . . . ?
C11 C12 C13 C8 0.1(4) . . . . ?
Cl1 C12 C13 C8 171.4(2) . . . . ?
Cl3 C12 C13 C8 -149.9(5) . . . . ?
N1 C14 C15 C16 -0.1(4) . . . . ?
O1 C14 C15 C16 178.9(2) . . . . ?
C14 C15 C16 C17 -0.7(3) . . . . ?
C15 C16 C17 N2 1.3(4) . . . . ?
C15 C16 C17 O2 -179.0(2) . . . . ?
C23 C18 C19 C20 -2.5(4) . . . . ?
O2 C18 C19 C20 172.0(3) . . . . ?
C23 C18 C19 Cl2 178.0(2) . . . . ?
O2 C18 C19 Cl2 -7.5(3) . . . . ?
C18 C19 C20 C21 -0.3(5) . . . . ?
Cl2 C19 C20 C21 179.2(2) . . . . ?
C19 C20 C21 C22 2.8(4) . . . . ?
C19 C20 C21 C24 -179.3(3) . . . . ?
C20 C21 C22 C23 -2.5(3) . . . . ?
C24 C21 C22 C23 179.6(2) . . . . ?
C19 C18 C23 C22 2.7(4) . . . . ?
O2 C18 C23 C22 -171.6(2) . . . . ?
C21 C22 C23 C18 -0.2(3) . . . . ?
C22 C21 C24 C26 -13.8(3) . . . . ?
C20 C21 C24 C26 168.3(2) . . . . ?
C22 C21 C24 C1 -134.7(2) . . . 3_666 ?
C20 C21 C24 C1 47.5(3) . . . 3_666 ?
C22 C21 C24 C25 105.6(2) . . . . ?
C20 C21 C24 C25 -72.2(3) . . . . ?
C21 C24 C25 C6 178.77(17) . . . 3_666 ?
C26 C24 C25 C6 -58.9(2) . . . 3_666 ?
C1 C24 C25 C6 57.8(2) 3_666 . . 3_666 ?
C21 C24 C26 C4 179.57(19) . . . 3_666 ?
C1 C24 C26 C4 -57.7(2) 3_666 . . 3_666 ?
C25 C24 C26 C4 59.6(2) . . . 3_666 ?
C29 C27 C28 C29 0.2(6) 3_655 . . . ?
C27 C28 C29 C27 -0.2(5) . . . 3_655 ?
C27 C28 C29 C30 179.5(3) . . . . ?
O1 C14 N1 N2 -178.6(2) . . . . ?
C15 C14 N1 N2 0.4(4) . . . . ?
O2 C17 N2 N1 179.3(2) . . . . ?
C16 C17 N2 N1 -1.1(4) . . . . ?
C14 N1 N2 C17 0.1(3) . . . . ?
N1 C14 O1 C11 -35.7(3) . . . . ?
C15 C14 O1 C11 145.2(2) . . . . ?
C12 C11 O1 C14 135.7(2) . . . . ?
C10 C11 O1 C14 -48.5(4) . . . . ?
N2 C17 O2 C18 6.2(3) . . . . ?
C16 C17 O2 C18 -173.4(2) . . . . ?
C19 C18 O2 C17 105.4(3) . . . . ?
C23 C18 O2 C17 -80.3(3) . . . . ?

_refine_diff_density_max         1.003
_refine_diff_density_min         -1.560
_refine_diff_density_rms         0.176

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1d
_database_code_depnum_ccdc_archive 'CCDC 2025178'
loop_
_audit_author_name
_audit_author_address
'Tadashi Hyodo'
;Tokushima Bunri University
Japan
;
_audit_update_record             
;
2020-08-25 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C59 H52 Cl4 N4 O4'
_chemical_formula_weight         1022.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.6415(17)
_cell_length_b                   11.1851(14)
_cell_length_c                   32.017(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4885.2(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             2136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.637
_shelx_estimated_absorpt_T_min   0.621
_shelx_estimated_absorpt_T_max   0.778
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7590
_exptl_absorpt_correction_T_max  0.8175
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            62640
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         4.258
_diffrn_reflns_theta_max         80.079
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5263
_reflns_number_gt                5118
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0944P)²+3.3748P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0106(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5263
_refine_ls_number_parameters     365
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0631
_refine_ls_wR_factor_ref         0.1887
_refine_ls_wR_factor_gt          0.1729
_refine_ls_goodness_of_fit_ref   1.288
_refine_ls_restrained_S_all      1.288
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C27 C 0.4862(5) 0.6026(8) 0.4980(2) 0.0450(16) Uani 0.500(0) 1 d . . P A -1
C28 C 0.4916(7) 0.5226(12) 0.4650(2) 0.0502(19) Uani 0.500(0) 1 d . . P A -1
H28 H 0.494498 0.552746 0.437281 0.060 Uiso 0.500(0) 1 calc R U P A -1
C29 C 0.4930(10) 0.4007(11) 0.4712(4) 0.075(3) Uani 0.500(0) 1 d . . P A -1
H29 H 0.496894 0.348693 0.447825 0.090 Uiso 0.500(0) 1 calc R U P A -1
C30 C 0.4888(7) 0.3528(10) 0.5111(4) 0.071(3) Uani 0.500(0) 1 d . . P A -1
H30 H 0.486918 0.268708 0.515305 0.085 Uiso 0.500(0) 1 calc R U P A -1
C31 C 0.4874(7) 0.4308(11) 0.5447(3) 0.062(3) Uani 0.500(0) 1 d . . P A -1
H31 H 0.488176 0.400330 0.572357 0.075 Uiso 0.500(0) 1 calc R U P A -1
C32 C 0.4848(7) 0.5518(12) 0.5381(3) 0.051(2) Uani 0.500(0) 1 d . . P A -1
H32 H 0.481940 0.603475 0.561586 0.062 Uiso 0.500(0) 1 calc R U P A -1
C33 C 0.4847(5) 0.7332(8) 0.4921(3) 0.0622(18) Uani 0.500(0) 1 d . . P A -1
H33A H 0.500139 0.752154 0.462963 0.093 Uiso 0.500(0) 1 calc R U P A -1
H33B H 0.533477 0.770352 0.510462 0.093 Uiso 0.500(0) 1 calc R U P A -1
H33C H 0.419411 0.764094 0.498990 0.093 Uiso 0.500(0) 1 calc R U P A -1
C1 C 0.62311(17) 0.40433(19) 0.70737(6) 0.0258(4) Uani 1 1 d . . . . .
H1A H 0.605140 0.352917 0.731352 0.031 Uiso 1 1 calc R U . . .
H1AB H 0.652655 0.352961 0.685568 0.031 Uiso 1 1 calc R U . . .
C2 C 0.69767(17) 0.4979(2) 0.72143(7) 0.0276(5) Uani 1 1 d . . . . .
H2 H 0.757521 0.456468 0.732207 0.033 Uiso 1 1 calc R U . . .
C3 C 0.72601(16) 0.5762(2) 0.68397(7) 0.0265(5) Uani 1 1 d . . . . .
H3A H 0.754707 0.525425 0.661775 0.032 Uiso 1 1 calc R U . . .
H3AB H 0.776187 0.635044 0.692677 0.032 Uiso 1 1 calc R U . . .
C4 C 0.63580(16) 0.64243(18) 0.66666(6) 0.0228(4) Uani 1 1 d . . . . .
C5 C 0.59102(17) 0.71751(18) 0.70250(6) 0.0255(4) Uani 1 1 d . . . . .
H5A H 0.639275 0.777858 0.711937 0.031 Uiso 1 1 calc R U . . .
H5AB H 0.532314 0.760309 0.692166 0.031 Uiso 1 1 calc R U . . .
C6 C 0.55980(15) 0.54729(17) 0.65304(6) 0.0210(4) Uani 1 1 d . . . . .
H6A H 0.500696 0.587853 0.642032 0.025 Uiso 1 1 calc R U . . .
H6AB H 0.587868 0.498015 0.630309 0.025 Uiso 1 1 calc R U . . .
C7 C 0.66126(17) 0.72295(19) 0.62964(7) 0.0265(5) Uani 1 1 d . . . . .
C8 C 0.75325(19) 0.7211(3) 0.61080(8) 0.0384(6) Uani 1 1 d . . . . .
H8 H 0.800386 0.664095 0.619770 0.046 Uiso 1 1 calc R U . . .
C9 C 0.7777(2) 0.8010(3) 0.57910(8) 0.0487(8) Uani 1 1 d . . . . .
H9 H 0.841444 0.799460 0.567173 0.058 Uiso 1 1 calc R U . . .
C10 C 0.7098(3) 0.8818(2) 0.56512(7) 0.0432(7) Uani 1 1 d . . . . .
C11 C 0.6158(3) 0.8792(2) 0.58102(8) 0.0454(7) Uani 1 1 d . . . . .
C12 C 0.5915(2) 0.8013(2) 0.61325(8) 0.0364(6) Uani 1 1 d . . . . .
H12 H 0.526786 0.801301 0.624213 0.044 Uiso 1 1 calc R U . . .
C13 C 0.7344(2) 0.9523(2) 0.49589(7) 0.0368(6) Uani 1 1 d . . . . .
C14 C 0.7564(2) 1.0504(2) 0.47051(8) 0.0404(6) Uani 1 1 d . . . . .
H14 H 0.771162 1.126719 0.481887 0.049 Uiso 1 1 calc R U . . .
C15 C 0.7555(2) 1.0304(2) 0.42859(7) 0.0337(5) Uani 1 1 d . . . . .
H15 H 0.770242 1.091807 0.409076 0.040 Uiso 1 1 calc R U . . .
C16 C 0.73159(17) 0.91428(19) 0.41582(7) 0.0263(5) Uani 1 1 d . . . . .
C17 C 0.66889(17) 0.80284(19) 0.35936(7) 0.0272(5) Uani 1 1 d . . . . .
C18 C 0.70475(17) 0.70917(19) 0.33608(7) 0.0262(5) Uani 1 1 d . . . . .
C19 C 0.64200(16) 0.62229(19) 0.31944(6) 0.0238(4) Uani 1 1 d . . . . .
H19 H 0.668297 0.558650 0.303298 0.029 Uiso 1 1 calc R U . . .
C20 C 0.54152(16) 0.62845(18) 0.32636(6) 0.0224(4) Uani 1 1 d . . . . .
C21 C 0.50728(18) 0.7239(2) 0.35045(8) 0.0333(5) Uani 1 1 d . . . . .
H21 H 0.439055 0.729522 0.356068 0.040 Uiso 1 1 calc R U . . .
C22 C 0.5691(2) 0.8105(2) 0.36636(8) 0.0354(5) Uani 1 1 d . . . . .
H22 H 0.543053 0.875107 0.382090 0.042 Uiso 1 1 calc R U . . .
C23 C 0.46978(16) 0.53480(18) 0.31012(6) 0.0218(4) Uani 1 1 d . . . . .
C24 C 0.51313(17) 0.45580(19) 0.27515(6) 0.0262(5) Uani 1 1 d . . . . .
H24A H 0.532376 0.506609 0.251198 0.031 Uiso 1 1 calc R U . . .
H24B H 0.572560 0.414694 0.285583 0.031 Uiso 1 1 calc R U . . .
C25 C 0.43758(18) 0.36249(19) 0.26074(6) 0.0275(5) Uani 1 1 d . . . . .
H25 H 0.467039 0.312180 0.238177 0.033 Uiso 1 1 calc R U . . .
C26 C 0.34586(19) 0.4248(2) 0.24384(7) 0.0309(5) Uani 1 1 d . . . . .
H26A H 0.363236 0.475310 0.219544 0.037 Uiso 1 1 calc R U . . .
H26B H 0.297303 0.364538 0.234637 0.037 Uiso 1 1 calc R U . . .
Cl2 Cl 0.82937(4) 0.69935(6) 0.32696(2) 0.0421(2) Uani 1 1 d . . . . .
N1 N 0.71278(18) 0.84491(17) 0.48273(6) 0.0337(5) Uani 1 1 d . . . . .
N2 N 0.71130(16) 0.82542(17) 0.44063(6) 0.0305(4) Uani 1 1 d . . . . .
O1 O 0.7362(2) 0.97321(18) 0.53772(6) 0.0592(7) Uani 1 1 d . . . . .
O2 O 0.73176(13) 0.89195(15) 0.37341(5) 0.0326(4) Uani 1 1 d . . . . .
Cl1A Cl 0.5080(10) 0.9590(6) 0.55769(10) 0.0482(17) Uani 0.52(2) 1 d . . P B 1
Cl1B Cl 0.5475(8) 0.9859(6) 0.56233(17) 0.0437(13) Uani 0.48(2) 1 d . . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C27 C28 1.387(12) . ?
C27 C32 1.402(12) . ?
C27 C33 1.474(11) . ?
C28 C29 1.378(14) . ?
C28 H28 0.9500 . ?
C29 C30 1.386(17) . ?
C29 H29 0.9500 . ?
C30 C31 1.384(16) . ?
C30 H30 0.9500 . ?
C31 C32 1.371(13) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C1 C2 1.527(3) . ?
C1 C23 1.544(3) 5_666 ?
C1 H1A 0.9900 . ?
C1 H1AB 0.9900 . ?
C2 C26 1.529(3) 5_666 ?
C2 C3 1.535(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.540(3) . ?
C3 H3A 0.9900 . ?
C3 H3AB 0.9900 . ?
C4 C7 1.529(3) . ?
C4 C5 1.548(3) . ?
C4 C6 1.548(3) . ?
C5 C25 1.529(3) 5_666 ?
C5 H5A 0.9900 . ?
C5 H5AB 0.9900 . ?
C6 C23 1.548(3) 5_666 ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C8 1.392(4) . ?
C7 C12 1.396(3) . ?
C8 C9 1.393(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.369(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.380(5) . ?
C10 O1 1.394(3) . ?
C11 C12 1.391(3) . ?
C11 Cl1B 1.627(5) . ?
C11 Cl1A 1.875(9) . ?
C12 H12 0.9500 . ?
C13 N1 1.307(3) . ?
C13 O1 1.360(3) . ?
C13 C14 1.398(3) . ?
C14 C15 1.361(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.400(3) . ?
C15 H15 0.9500 . ?
C16 N2 1.302(3) . ?
C16 O2 1.381(3) . ?
C17 C18 1.376(3) . ?
C17 C22 1.383(4) . ?
C17 O2 1.390(3) . ?
C18 C19 1.400(3) . ?
C18 Cl2 1.728(2) . ?
C19 C20 1.390(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.398(3) . ?
C20 C23 1.525(3) . ?
C21 C22 1.381(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C23 C24 1.544(3) . ?
C24 C25 1.538(3) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.531(3) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
N1 N2 1.366(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C28 C27 C32 115.9(8) . . ?
C28 C27 C33 122.8(9) . . ?
C32 C27 C33 121.2(8) . . ?
C29 C28 C27 121.9(9) . . ?
C29 C28 H28 119.1 . . ?
C27 C28 H28 119.1 . . ?
C28 C29 C30 121.0(11) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 H29 119.5 . . ?
C31 C30 C29 118.1(10) . . ?
C31 C30 H30 120.9 . . ?
C29 C30 H30 120.9 . . ?
C32 C31 C30 120.2(10) . . ?
C32 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?
C31 C32 C27 122.7(10) . . ?
C31 C32 H32 118.6 . . ?
C27 C32 H32 118.6 . . ?
C27 C33 H33A 109.5 . . ?
C27 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C27 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C2 C1 C23 110.58(17) . 5_666 ?
C2 C1 H1A 109.5 . . ?
C23 C1 H1A 109.5 5_666 . ?
C2 C1 H1AB 109.5 . . ?
C23 C1 H1AB 109.5 5_666 . ?
H1A C1 H1AB 108.1 . . ?
C1 C2 C26 110.07(19) . 5_666 ?
C1 C2 C3 109.17(17) . . ?
C26 C2 C3 110.10(18) 5_666 . ?
C1 C2 H2 109.2 . . ?
C26 C2 H2 109.2 5_666 . ?
C3 C2 H2 109.2 . . ?
C2 C3 C4 110.77(18) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3AB 109.5 . . ?
C4 C3 H3AB 109.5 . . ?
H3A C3 H3AB 108.1 . . ?
C7 C4 C3 112.40(18) . . ?
C7 C4 C5 110.17(17) . . ?
C3 C4 C5 108.05(17) . . ?
C7 C4 C6 109.80(16) . . ?
C3 C4 C6 107.80(17) . . ?
C5 C4 C6 108.51(17) . . ?
C25 C5 C4 110.72(17) 5_666 . ?
C25 C5 H5A 109.5 5_666 . ?
C4 C5 H5A 109.5 . . ?
C25 C5 H5AB 109.5 5_666 . ?
C4 C5 H5AB 109.5 . . ?
H5A C5 H5AB 108.1 . . ?
C23 C6 C4 111.56(16) 5_666 . ?
C23 C6 H6A 109.3 5_666 . ?
C4 C6 H6A 109.3 . . ?
C23 C6 H6AB 109.3 5_666 . ?
C4 C6 H6AB 109.3 . . ?
H6A C6 H6AB 108.0 . . ?
C8 C7 C12 117.4(2) . . ?
C8 C7 C4 122.1(2) . . ?
C12 C7 C4 120.4(2) . . ?
C7 C8 C9 121.5(3) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C11 119.6(2) . . ?
C9 C10 O1 121.0(3) . . ?
C11 C10 O1 119.2(3) . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 Cl1B 112.4(4) . . ?
C12 C11 Cl1B 126.6(4) . . ?
C10 C11 Cl1A 124.9(3) . . ?
C12 C11 Cl1A 114.0(4) . . ?
C11 C12 C7 120.7(3) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
N1 C13 O1 118.7(2) . . ?
N1 C13 C14 125.6(2) . . ?
O1 C13 C14 115.7(2) . . ?
C15 C14 C13 116.3(2) . . ?
C15 C14 H14 121.9 . . ?
C13 C14 H14 121.9 . . ?
C14 C15 C16 116.3(2) . . ?
C14 C15 H15 121.9 . . ?
C16 C15 H15 121.9 . . ?
N2 C16 O2 117.53(19) . . ?
N2 C16 C15 125.4(2) . . ?
O2 C16 C15 117.03(19) . . ?
C18 C17 C22 119.0(2) . . ?
C18 C17 O2 120.1(2) . . ?
C22 C17 O2 120.7(2) . . ?
C17 C18 C19 121.2(2) . . ?
C17 C18 Cl2 119.32(18) . . ?
C19 C18 Cl2 119.52(17) . . ?
C20 C19 C18 120.5(2) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 117.1(2) . . ?
C19 C20 C23 122.98(18) . . ?
C21 C20 C23 119.9(2) . . ?
C22 C21 C20 122.4(2) . . ?
C22 C21 H21 118.8 . . ?
C20 C21 H21 118.8 . . ?
C21 C22 C17 119.9(2) . . ?
C21 C22 H22 120.1 . . ?
C17 C22 H22 120.1 . . ?
C20 C23 C1 110.34(17) . 5_666 ?
C20 C23 C24 113.24(18) . . ?
C1 C23 C24 107.67(17) 5_666 . ?
C20 C23 C6 108.35(16) . 5_666 ?
C1 C23 C6 108.91(17) 5_666 5_666 ?
C24 C23 C6 108.23(16) . 5_666 ?
C25 C24 C23 110.45(18) . . ?
C25 C24 H24A 109.6 . . ?
C23 C24 H24A 109.6 . . ?
C25 C24 H24B 109.6 . . ?
C23 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
C5 C25 C26 109.27(19) 5_666 . ?
C5 C25 C24 109.71(17) 5_666 . ?
C26 C25 C24 110.16(18) . . ?
C5 C25 H25 109.2 5_666 . ?
C26 C25 H25 109.2 . . ?
C24 C25 H25 109.2 . . ?
C2 C26 C25 108.54(17) 5_666 . ?
C2 C26 H26A 110.0 5_666 . ?
C25 C26 H26A 110.0 . . ?
C2 C26 H26B 110.0 5_666 . ?
C25 C26 H26B 110.0 . . ?
H26A C26 H26B 108.4 . . ?
C13 N1 N2 117.92(19) . . ?
C16 N2 N1 118.50(18) . . ?
C13 O1 C10 119.29(19) . . ?
C16 O2 C17 116.55(17) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C32 C27 C28 C29 1.6(13) . . . . ?
C33 C27 C28 C29 180.0(9) . . . . ?
C27 C28 C29 C30 0.1(17) . . . . ?
C28 C29 C30 C31 -2.7(16) . . . . ?
C29 C30 C31 C32 3.5(14) . . . . ?
C30 C31 C32 C27 -1.8(14) . . . . ?
C28 C27 C32 C31 -0.8(13) . . . . ?
C33 C27 C32 C31 -179.2(8) . . . . ?
C23 C1 C2 C26 61.1(2) 5_666 . . 5_666 ?
C23 C1 C2 C3 -59.9(2) 5_666 . . . ?
C1 C2 C3 C4 61.2(2) . . . . ?
C26 C2 C3 C4 -59.7(2) 5_666 . . . ?
C2 C3 C4 C7 179.15(17) . . . . ?
C2 C3 C4 C5 57.4(2) . . . . ?
C2 C3 C4 C6 -59.7(2) . . . . ?
C7 C4 C5 C25 178.34(18) . . . 5_666 ?
C3 C4 C5 C25 -58.5(2) . . . 5_666 ?
C6 C4 C5 C25 58.1(2) . . . 5_666 ?
C7 C4 C6 C23 -178.83(17) . . . 5_666 ?
C3 C4 C6 C23 58.4(2) . . . 5_666 ?
C5 C4 C6 C23 -58.4(2) . . . 5_666 ?
C3 C4 C7 C8 8.6(3) . . . . ?
C5 C4 C7 C8 129.1(2) . . . . ?
C6 C4 C7 C8 -111.4(2) . . . . ?
C3 C4 C7 C12 -171.9(2) . . . . ?
C5 C4 C7 C12 -51.4(3) . . . . ?
C6 C4 C7 C12 68.1(2) . . . . ?
C12 C7 C8 C9 5.2(4) . . . . ?
C4 C7 C8 C9 -175.3(2) . . . . ?
C7 C8 C9 C10 -1.6(4) . . . . ?
C8 C9 C10 C11 -3.5(4) . . . . ?
C8 C9 C10 O1 171.0(2) . . . . ?
C9 C10 C11 C12 4.8(4) . . . . ?
O1 C10 C11 C12 -169.8(2) . . . . ?
C9 C10 C11 Cl1B 177.2(5) . . . . ?
O1 C10 C11 Cl1B 2.6(5) . . . . ?
C9 C10 C11 Cl1A -166.0(4) . . . . ?
O1 C10 C11 Cl1A 19.4(5) . . . . ?
C10 C11 C12 C7 -1.0(4) . . . . ?
Cl1B C11 C12 C7 -172.3(6) . . . . ?
Cl1A C11 C12 C7 170.7(3) . . . . ?
C8 C7 C12 C11 -3.9(4) . . . . ?
C4 C7 C12 C11 176.6(2) . . . . ?
N1 C13 C14 C15 -0.4(5) . . . . ?
O1 C13 C14 C15 179.6(3) . . . . ?
C13 C14 C15 C16 0.6(4) . . . . ?
C14 C15 C16 N2 -0.6(4) . . . . ?
C14 C15 C16 O2 -179.1(2) . . . . ?
C22 C17 C18 C19 0.1(3) . . . . ?
O2 C17 C18 C19 -176.06(19) . . . . ?
C22 C17 C18 Cl2 179.68(18) . . . . ?
O2 C17 C18 Cl2 3.5(3) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
Cl2 C18 C19 C20 -179.96(16) . . . . ?
C18 C19 C20 C21 -0.2(3) . . . . ?
C18 C19 C20 C23 -178.25(18) . . . . ?
C19 C20 C21 C22 1.1(4) . . . . ?
C23 C20 C21 C22 179.2(2) . . . . ?
C20 C21 C22 C17 -1.4(4) . . . . ?
C18 C17 C22 C21 0.7(4) . . . . ?
O2 C17 C22 C21 176.9(2) . . . . ?
C19 C20 C23 C1 -138.0(2) . . . 5_666 ?
C21 C20 C23 C1 44.0(3) . . . 5_666 ?
C19 C20 C23 C24 -17.2(3) . . . . ?
C21 C20 C23 C24 164.8(2) . . . . ?
C19 C20 C23 C6 102.9(2) . . . 5_666 ?
C21 C20 C23 C6 -75.1(2) . . . 5_666 ?
C20 C23 C24 C25 179.18(17) . . . . ?
C1 C23 C24 C25 -58.5(2) 5_666 . . . ?
C6 C23 C24 C25 59.0(2) 5_666 . . . ?
C23 C24 C25 C5 -60.2(2) . . . 5_666 ?
C23 C24 C25 C26 60.2(2) . . . . ?
C5 C25 C26 C2 61.1(2) 5_666 . . 5_666 ?
C24 C25 C26 C2 -59.5(2) . . . 5_666 ?
O1 C13 N1 N2 -180.0(3) . . . . ?
C14 C13 N1 N2 0.0(5) . . . . ?
O2 C16 N2 N1 178.6(2) . . . . ?
C15 C16 N2 N1 0.1(4) . . . . ?
C13 N1 N2 C16 0.2(4) . . . . ?
N1 C13 O1 C10 -3.5(5) . . . . ?
C14 C13 O1 C10 176.5(3) . . . . ?
C9 C10 O1 C13 87.6(4) . . . . ?
C11 C10 O1 C13 -97.9(3) . . . . ?
N2 C16 O2 C17 29.9(3) . . . . ?
C15 C16 O2 C17 -151.5(2) . . . . ?
C18 C17 O2 C16 -125.3(2) . . . . ?
C22 C17 O2 C16 58.6(3) . . . . ?

_refine_diff_density_max         0.827
_refine_diff_density_min         -0.804
_refine_diff_density_rms         0.246

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1f
_database_code_depnum_ccdc_archive 'CCDC 2025180'
loop_
_audit_author_name
_audit_author_address
'Tadashi Hyodo'
;Tokushima Bunri University
Japan
;
_audit_update_record             
;
2020-08-25 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H48 Cl8 N4 O4'
_chemical_formula_weight         1100.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.397(4)
_cell_length_b                   13.840(3)
_cell_length_c                   11.647(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.793(3)
_cell_angle_gamma                90
_cell_volume                     2502.1(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6866
_cell_measurement_theta_min      2.21
_cell_measurement_theta_max      26.82

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.502
_shelx_estimated_absorpt_T_min   0.864
_shelx_estimated_absorpt_T_max   0.951
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            22485
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.312
_diffrn_reflns_theta_max         26.132
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4644
_reflns_number_gt                3020
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2004)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0901P)²+2.0475P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4644
_refine_ls_number_parameters     344
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0983
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1754
_refine_ls_wR_factor_gt          0.1480
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0336(2) 0.3299(3) 0.8496(3) 0.0240(8) Uani 1 1 d . . . . .
H1 H 0.012899 0.274854 0.888467 0.029 Uiso 1 1 calc R U . . .
C2 C -0.0437(2) 0.3786(3) 0.7568(3) 0.0282(9) Uani 1 1 d . . . . .
H2A H -0.075021 0.331172 0.694518 0.034 Uiso 1 1 calc R U . . .
H2AB H -0.083837 0.403513 0.797635 0.034 Uiso 1 1 calc R U . . .
C3 C -0.0108(2) 0.4618(3) 0.6971(3) 0.0242(8) Uani 1 1 d . . . . .
H3 H -0.060822 0.493692 0.635780 0.029 Uiso 1 1 calc R U . . .
C4 C 0.0511(2) 0.4244(3) 0.6346(3) 0.0224(8) Uani 1 1 d . . . . .
H4A H 0.070617 0.478703 0.594635 0.027 Uiso 1 1 calc R U . . .
H4AB H 0.021109 0.377103 0.571314 0.027 Uiso 1 1 calc R U . . .
C5 C 0.1304(2) 0.3754(2) 0.7273(3) 0.0213(8) Uani 1 1 d . . . . .
C6 C 0.0965(2) 0.2919(3) 0.7879(3) 0.0262(8) Uani 1 1 d . . . . .
H6A H 0.067115 0.243504 0.725733 0.031 Uiso 1 1 calc R U . . .
H6AB H 0.145516 0.259734 0.848711 0.031 Uiso 1 1 calc R U . . .
C7 C 0.0795(2) 0.4034(3) 0.9467(3) 0.0246(8) Uani 1 1 d . . . . .
H7A H 0.128409 0.371719 1.008430 0.030 Uiso 1 1 calc R U . . .
H7AB H 0.039117 0.427394 0.987666 0.030 Uiso 1 1 calc R U . . .
C8 C 0.0359(2) 0.5362(2) 0.7939(3) 0.0209(8) Uani 1 1 d . . . . .
H8A H -0.004635 0.562187 0.833455 0.025 Uiso 1 1 calc R U . . .
H8AB H 0.056052 0.590606 0.754901 0.025 Uiso 1 1 calc R U . . .
C9 C 0.1750(2) 0.4500(2) 0.8255(3) 0.0196(8) Uani 1 1 d . . . . .
H9A H 0.196468 0.504190 0.787807 0.023 Uiso 1 1 calc R U . . .
H9AB H 0.225161 0.419363 0.886124 0.023 Uiso 1 1 calc R U . . .
C10 C 0.1950(2) 0.3421(2) 0.6665(3) 0.0222(8) Uani 1 1 d . . . . .
C11 C 0.2123(2) 0.3994(3) 0.5789(3) 0.0277(9) Uani 1 1 d . . . . .
H11 H 0.181430 0.457999 0.554725 0.033 Uiso 1 1 calc R U . . .
C12 C 0.2733(2) 0.3731(3) 0.5263(3) 0.0296(9) Uani 1 1 d . . . . .
C13 C 0.3193(2) 0.2879(3) 0.5600(3) 0.0289(9) Uani 1 1 d . . . . .
C14 C 0.3045(2) 0.2315(3) 0.6478(4) 0.0304(9) Uani 1 1 d . . . . .
H14 H 0.336654 0.173839 0.673096 0.036 Uiso 1 1 calc R U . . .
C15 C 0.2429(2) 0.2580(3) 0.7004(3) 0.0258(8) Uani 1 1 d . . . . .
H15 H 0.233245 0.217747 0.760807 0.031 Uiso 1 1 calc R U . . .
C16 C 0.4608(2) 0.2597(3) 0.5530(3) 0.0247(8) Uani 1 1 d . . . . .
C17 C 0.5118(2) 0.2386(3) 0.4808(3) 0.0280(9) Uani 1 1 d . . . . .
H17 H 0.487206 0.224993 0.396676 0.034 Uiso 1 1 calc R U . . .
C18 C 0.5985(2) 0.2385(3) 0.5369(3) 0.0272(9) Uani 1 1 d . . . . .
H18 H 0.637790 0.224278 0.494420 0.033 Uiso 1 1 calc R U . . .
C19 C 0.6268(2) 0.2606(2) 0.6615(3) 0.0221(8) Uani 1 1 d . . . . .
C20 C 0.7486(2) 0.3185(3) 0.8183(3) 0.0231(8) Uani 1 1 d . . . . .
C21 C 0.8158(2) 0.2842(3) 0.9139(3) 0.0251(8) Uani 1 1 d . . . . .
C22 C 0.8604(2) 0.3442(3) 1.0088(3) 0.0232(8) Uani 1 1 d . . . . .
H22 H 0.906871 0.318806 1.073566 0.028 Uiso 1 1 calc R U . . .
C23 C 0.8381(2) 0.4405(2) 1.0103(3) 0.0212(8) Uani 1 1 d . . . . .
C24 C 0.7681(2) 0.4733(3) 0.9149(3) 0.0274(8) Uani 1 1 d . . . . .
H24 H 0.750192 0.538573 0.915159 0.033 Uiso 1 1 calc R U . . .
C25 C 0.7239(2) 0.4141(3) 0.8201(3) 0.0284(9) Uani 1 1 d . . . . .
H25 H 0.676603 0.438810 0.756037 0.034 Uiso 1 1 calc R U . . .
C26 C 0.8867(2) 0.5104(2) 1.1099(3) 0.0207(8) Uani 1 1 d . . . . .
N1 N 0.48960(18) 0.2803(2) 0.6689(3) 0.0248(7) Uani 1 1 d . . . . .
N2 N 0.57672(18) 0.2804(2) 0.7255(3) 0.0261(7) Uani 1 1 d . . . . .
O1 O 0.37363(15) 0.2592(2) 0.4960(2) 0.0347(7) Uani 1 1 d . . . . .
O2 O 0.71361(15) 0.25863(19) 0.7184(2) 0.0298(6) Uani 1 1 d . . . . .
Cl1 Cl 0.29093(8) 0.44717(8) 0.41743(11) 0.0505(3) Uani 1 1 d . . . . .
Cl2 Cl 0.84628(6) 0.16462(7) 0.91130(10) 0.0396(3) Uani 1 1 d . . . . .
C27 C 0.4941(7) 0.5086(8) 0.1799(9) 0.049(2) Uani 0.719(4) 1 d . . P A 1
H27A H 0.469562 0.574531 0.172730 0.059 Uiso 0.719(4) 1 calc R U P A 1
H27B H 0.456872 0.469717 0.111641 0.059 Uiso 0.719(4) 1 calc R U P A 1
Cl3 Cl 0.49257(16) 0.45843(18) 0.3139(3) 0.0572(6) Uani 0.719(4) 1 d . . P A 1
Cl4 Cl 0.59896(11) 0.51497(15) 0.16757(18) 0.0620(7) Uani 0.719(4) 1 d . . P A
1
C28 C 0.5608(10) 0.4845(13) 0.2892(15) 0.049(4) Uani 0.281(4) 1 d . . P A 2
H28A H 0.593198 0.546030 0.307389 0.058 Uiso 0.281(4) 1 calc R U P A 2
H28B H 0.603007 0.430843 0.305845 0.058 Uiso 0.281(4) 1 calc R U P A 2
Cl5 Cl 0.4974(6) 0.4822(5) 0.1362(7) 0.062(2) Uani 0.281(4) 1 d . . P A 2
Cl6 Cl 0.4953(4) 0.4729(4) 0.3837(8) 0.0630(18) Uani 0.281(4) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.527(5) . ?
C1 C7 1.527(5) . ?
C1 C2 1.531(5) . ?
C1 H1 1.0000 . ?
C2 C3 1.530(5) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.519(5) . ?
C3 C8 1.536(5) . ?
C3 H3 1.0000 . ?
C4 C5 1.553(5) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C10 1.523(5) . ?
C5 C9 1.539(5) . ?
C5 C6 1.548(5) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C26 1.549(5) 3_667 ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C26 1.538(4) 3_667 ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C26 1.542(5) 3_667 ?
C9 H9A 0.9900 . ?
C9 H9AB 0.9900 . ?
C10 C15 1.387(5) . ?
C10 C11 1.392(5) . ?
C11 C12 1.378(5) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(5) . ?
C12 Cl1 1.726(4) . ?
C13 C14 1.369(5) . ?
C13 O1 1.391(4) . ?
C14 C15 1.389(5) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 N1 1.310(4) . ?
C16 O1 1.369(4) . ?
C16 C17 1.394(5) . ?
C17 C18 1.361(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.408(5) . ?
C18 H18 0.9500 . ?
C19 N2 1.303(4) . ?
C19 O2 1.363(4) . ?
C20 C21 1.374(5) . ?
C20 C25 1.386(5) . ?
C20 O2 1.392(4) . ?
C21 C22 1.387(5) . ?
C21 Cl2 1.732(4) . ?
C22 C23 1.383(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.392(5) . ?
C23 C26 1.524(5) . ?
C24 C25 1.379(5) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N1 N2 1.367(4) . ?
C27 Cl3 1.716(10) . ?
C27 Cl4 1.774(11) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 Cl5 1.751(17) . ?
C28 Cl6 1.776(17) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C7 109.3(3) . . ?
C6 C1 C2 110.5(3) . . ?
C7 C1 C2 109.2(3) . . ?
C6 C1 H1 109.3 . . ?
C7 C1 H1 109.3 . . ?
C2 C1 H1 109.3 . . ?
C3 C2 C1 108.6(3) . . ?
C3 C2 H2A 110.0 . . ?
C1 C2 H2A 110.0 . . ?
C3 C2 H2AB 110.0 . . ?
C1 C2 H2AB 110.0 . . ?
H2A C2 H2AB 108.4 . . ?
C4 C3 C2 110.4(3) . . ?
C4 C3 C8 109.1(3) . . ?
C2 C3 C8 109.7(3) . . ?
C4 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
C8 C3 H3 109.2 . . ?
C3 C4 C5 110.8(3) . . ?
C3 C4 H4A 109.5 . . ?
C5 C4 H4A 109.5 . . ?
C3 C4 H4AB 109.5 . . ?
C5 C4 H4AB 109.5 . . ?
H4A C4 H4AB 108.1 . . ?
C10 C5 C9 108.3(3) . . ?
C10 C5 C6 113.1(3) . . ?
C9 C5 C6 108.4(3) . . ?
C10 C5 C4 111.2(3) . . ?
C9 C5 C4 108.4(3) . . ?
C6 C5 C4 107.4(3) . . ?
C1 C6 C5 110.7(3) . . ?
C1 C6 H6A 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C1 C6 H6AB 109.5 . . ?
C5 C6 H6AB 109.5 . . ?
H6A C6 H6AB 108.1 . . ?
C1 C7 C26 110.8(3) . 3_667 ?
C1 C7 H7A 109.5 . . ?
C26 C7 H7A 109.5 3_667 . ?
C1 C7 H7AB 109.5 . . ?
C26 C7 H7AB 109.5 3_667 . ?
H7A C7 H7AB 108.1 . . ?
C3 C8 C26 110.7(3) . 3_667 ?
C3 C8 H8A 109.5 . . ?
C26 C8 H8A 109.5 3_667 . ?
C3 C8 H8AB 109.5 . . ?
C26 C8 H8AB 109.5 3_667 . ?
H8A C8 H8AB 108.1 . . ?
C5 C9 C26 111.8(3) . 3_667 ?
C5 C9 H9A 109.3 . . ?
C26 C9 H9A 109.3 3_667 . ?
C5 C9 H9AB 109.3 . . ?
C26 C9 H9AB 109.3 3_667 . ?
H9A C9 H9AB 107.9 . . ?
C15 C10 C11 117.1(3) . . ?
C15 C10 C5 122.4(3) . . ?
C11 C10 C5 120.3(3) . . ?
C12 C11 C10 121.6(4) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C11 C12 C13 120.3(4) . . ?
C11 C12 Cl1 119.1(3) . . ?
C13 C12 Cl1 120.6(3) . . ?
C14 C13 C12 119.0(3) . . ?
C14 C13 O1 122.5(4) . . ?
C12 C13 O1 118.3(3) . . ?
C13 C14 C15 120.6(4) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C10 C15 C14 121.4(4) . . ?
C10 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
N1 C16 O1 118.3(3) . . ?
N1 C16 C17 125.5(3) . . ?
O1 C16 C17 116.2(3) . . ?
C18 C17 C16 116.6(3) . . ?
C18 C17 H17 121.7 . . ?
C16 C17 H17 121.7 . . ?
C17 C18 C19 116.2(3) . . ?
C17 C18 H18 121.9 . . ?
C19 C18 H18 121.9 . . ?
N2 C19 O2 118.5(3) . . ?
N2 C19 C18 125.2(3) . . ?
O2 C19 C18 116.2(3) . . ?
C21 C20 C25 118.6(3) . . ?
C21 C20 O2 118.6(3) . . ?
C25 C20 O2 122.5(3) . . ?
C20 C21 C22 121.2(3) . . ?
C20 C21 Cl2 118.4(3) . . ?
C22 C21 Cl2 120.3(3) . . ?
C23 C22 C21 120.8(3) . . ?
C23 C22 H22 119.6 . . ?
C21 C22 H22 119.6 . . ?
C22 C23 C24 117.3(3) . . ?
C22 C23 C26 123.1(3) . . ?
C24 C23 C26 119.6(3) . . ?
C25 C24 C23 122.1(3) . . ?
C25 C24 H24 119.0 . . ?
C23 C24 H24 119.0 . . ?
C24 C25 C20 119.9(3) . . ?
C24 C25 H25 120.0 . . ?
C20 C25 H25 120.0 . . ?
C23 C26 C8 113.2(3) . 3_667 ?
C23 C26 C9 109.5(3) . 3_667 ?
C8 C26 C9 108.1(3) 3_667 3_667 ?
C23 C26 C7 109.6(3) . 3_667 ?
C8 C26 C7 108.0(3) 3_667 3_667 ?
C9 C26 C7 108.3(3) 3_667 3_667 ?
C16 N1 N2 118.1(3) . . ?
C19 N2 N1 118.5(3) . . ?
C16 O1 C13 119.2(3) . . ?
C19 O2 C20 118.6(3) . . ?
Cl3 C27 Cl4 113.1(6) . . ?
Cl3 C27 H27A 109.0 . . ?
Cl4 C27 H27A 109.0 . . ?
Cl3 C27 H27B 109.0 . . ?
Cl4 C27 H27B 109.0 . . ?
H27A C27 H27B 107.8 . . ?
Cl5 C28 Cl6 110.5(10) . . ?
Cl5 C28 H28A 109.6 . . ?
Cl6 C28 H28A 109.6 . . ?
Cl5 C28 H28B 109.6 . . ?
Cl6 C28 H28B 109.6 . . ?
H28A C28 H28B 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -59.1(4) . . . . ?
C7 C1 C2 C3 61.2(4) . . . . ?
C1 C2 C3 C4 59.4(4) . . . . ?
C1 C2 C3 C8 -60.9(4) . . . . ?
C2 C3 C4 C5 -60.7(4) . . . . ?
C8 C3 C4 C5 60.0(4) . . . . ?
C3 C4 C5 C10 -177.2(3) . . . . ?
C3 C4 C5 C9 -58.3(4) . . . . ?
C3 C4 C5 C6 58.6(4) . . . . ?
C7 C1 C6 C5 -60.0(4) . . . . ?
C2 C1 C6 C5 60.1(4) . . . . ?
C10 C5 C6 C1 178.8(3) . . . . ?
C9 C5 C6 C1 58.7(4) . . . . ?
C4 C5 C6 C1 -58.2(4) . . . . ?
C6 C1 C7 C26 60.0(4) . . . 3_667 ?
C2 C1 C7 C26 -61.0(4) . . . 3_667 ?
C4 C3 C8 C26 -60.7(4) . . . 3_667 ?
C2 C3 C8 C26 60.3(4) . . . 3_667 ?
C10 C5 C9 C26 178.7(3) . . . 3_667 ?
C6 C5 C9 C26 -58.3(4) . . . 3_667 ?
C4 C5 C9 C26 58.0(4) . . . 3_667 ?
C9 C5 C10 C15 96.6(4) . . . . ?
C6 C5 C10 C15 -23.5(5) . . . . ?
C4 C5 C10 C15 -144.4(3) . . . . ?
C9 C5 C10 C11 -79.1(4) . . . . ?
C6 C5 C10 C11 160.8(3) . . . . ?
C4 C5 C10 C11 39.9(4) . . . . ?
C15 C10 C11 C12 1.1(5) . . . . ?
C5 C10 C11 C12 177.1(3) . . . . ?
C10 C11 C12 C13 -0.1(6) . . . . ?
C10 C11 C12 Cl1 179.6(3) . . . . ?
C11 C12 C13 C14 -1.3(5) . . . . ?
Cl1 C12 C13 C14 179.1(3) . . . . ?
C11 C12 C13 O1 173.5(3) . . . . ?
Cl1 C12 C13 O1 -6.1(5) . . . . ?
C12 C13 C14 C15 1.5(5) . . . . ?
O1 C13 C14 C15 -173.1(3) . . . . ?
C11 C10 C15 C14 -0.9(5) . . . . ?
C5 C10 C15 C14 -176.7(3) . . . . ?
C13 C14 C15 C10 -0.4(5) . . . . ?
N1 C16 C17 C18 0.9(6) . . . . ?
O1 C16 C17 C18 -179.7(3) . . . . ?
C16 C17 C18 C19 -0.5(5) . . . . ?
C17 C18 C19 N2 0.2(6) . . . . ?
C17 C18 C19 O2 178.8(3) . . . . ?
C25 C20 C21 C22 -2.3(5) . . . . ?
O2 C20 C21 C22 171.7(3) . . . . ?
C25 C20 C21 Cl2 179.9(3) . . . . ?
O2 C20 C21 Cl2 -6.0(5) . . . . ?
C20 C21 C22 C23 0.5(6) . . . . ?
Cl2 C21 C22 C23 178.2(3) . . . . ?
C21 C22 C23 C24 1.7(5) . . . . ?
C21 C22 C23 C26 -177.9(3) . . . . ?
C22 C23 C24 C25 -2.2(5) . . . . ?
C26 C23 C24 C25 177.5(3) . . . . ?
C23 C24 C25 C20 0.4(6) . . . . ?
C21 C20 C25 C24 1.8(5) . . . . ?
O2 C20 C25 C24 -171.9(3) . . . . ?
C22 C23 C26 C8 1.6(5) . . . 3_667 ?
C24 C23 C26 C8 -178.0(3) . . . 3_667 ?
C22 C23 C26 C9 -119.1(4) . . . 3_667 ?
C24 C23 C26 C9 61.3(4) . . . 3_667 ?
C22 C23 C26 C7 122.3(4) . . . 3_667 ?
C24 C23 C26 C7 -57.4(4) . . . 3_667 ?
O1 C16 N1 N2 179.8(3) . . . . ?
C17 C16 N1 N2 -0.8(6) . . . . ?
O2 C19 N2 N1 -178.6(3) . . . . ?
C18 C19 N2 N1 -0.1(5) . . . . ?
C16 N1 N2 C19 0.4(5) . . . . ?
N1 C16 O1 C13 5.0(5) . . . . ?
C17 C16 O1 C13 -174.4(3) . . . . ?
C14 C13 O1 C16 -73.2(5) . . . . ?
C12 C13 O1 C16 112.2(4) . . . . ?
N2 C19 O2 C20 -30.3(5) . . . . ?
C18 C19 O2 C20 151.0(3) . . . . ?
C21 C20 O2 C19 142.3(3) . . . . ?
C25 C20 O2 C19 -43.9(5) . . . . ?

_refine_diff_density_max         0.573
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.076

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1e
_database_code_depnum_ccdc_archive 'CCDC 2025179'
loop_
_audit_author_name
_audit_author_address
'Tadashi Hyodo'
;Tokushima Bunri University
Japan
;
_audit_update_record             
;
2020-08-25 deposited with the CCDC.	2020-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C54 H46 Cl10 N4 O4'
_chemical_formula_weight         1169.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   11.8817(5)
_cell_length_b                   13.9512(6)
_cell_length_c                   30.8666(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5116.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9742
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      78.44

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_F_000             2400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    5.409
_shelx_estimated_absorpt_T_min   0.614
_shelx_estimated_absorpt_T_max   0.774
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.7580
_exptl_absorpt_correction_T_max  0.8866
_exptl_absorpt_process_details   'SADABS Sheldrick 1996'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_measurement_device_type  'BrukerD8 goniometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            60546
_diffrn_reflns_av_unetI/netI     0.0780
_diffrn_reflns_av_R_equivalents  0.0815
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         3.476
_diffrn_reflns_theta_max         79.769
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10784
_reflns_number_gt                7493
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.809
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 (Bruker AXS, 2015)'
_computing_cell_refinement       'SAINT (Bruker AXS, 2015)'
_computing_data_reduction        'SAINT (Bruker AXS, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'SHELXLE (Hübschle et al., 2011)'
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0692P)²+3.5107P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_chemical_absolute_configuration ?
_refine_ls_number_reflns         10784
_refine_ls_number_parameters     659
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1019
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1537
_refine_ls_wR_factor_gt          0.1336
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8265(6) 0.8720(4) 0.56148(17) 0.0299(14) Uani 1 1 d . . . . .
C2 C 0.7535(6) 0.9554(5) 0.54470(19) 0.0368(16) Uani 1 1 d . . . . .
H2A H 0.719135 0.989410 0.569556 0.044 Uiso 1 1 calc R U . . .
H2AB H 0.801434 1.001548 0.528794 0.044 Uiso 1 1 calc R U . . .
C3 C 0.6606(6) 0.9185(5) 0.51468(18) 0.0388(17) Uani 1 1 d . . . . .
H3 H 0.613943 0.973792 0.504606 0.047 Uiso 1 1 calc R U . . .
C4 C 0.5863(6) 0.8487(5) 0.53977(18) 0.0337(15) Uani 1 1 d . . . . .
H4A H 0.524888 0.825812 0.520713 0.040 Uiso 1 1 calc R U . . .
H4AB H 0.551723 0.882406 0.564664 0.040 Uiso 1 1 calc R U . . .
C5 C 0.6543(5) 0.7623(4) 0.55635(16) 0.0267(13) Uani 1 1 d . . . . .
C6 C 0.7494(5) 0.8004(4) 0.58590(16) 0.0256(13) Uani 1 1 d . . . . .
H6A H 0.795058 0.745831 0.596461 0.031 Uiso 1 1 calc R U . . .
H6AB H 0.715854 0.832657 0.611378 0.031 Uiso 1 1 calc R U . . .
C7 C 0.8760(6) 0.8193(5) 0.52170(17) 0.0364(16) Uani 1 1 d . . . . .
H7A H 0.925847 0.863465 0.505526 0.044 Uiso 1 1 calc R U . . .
H7AB H 0.921865 0.764274 0.531623 0.044 Uiso 1 1 calc R U . . .
C8 C 0.7127(7) 0.8686(5) 0.47538(19) 0.0464(19) Uani 1 1 d . . . . .
H8A H 0.761414 0.913883 0.459341 0.056 Uiso 1 1 calc R U . . .
H8AB H 0.652622 0.846100 0.455593 0.056 Uiso 1 1 calc R U . . .
C9 C 0.7823(6) 0.7831(5) 0.49151(18) 0.0383(16) Uani 1 1 d . . . . .
H9 H 0.816767 0.749487 0.466169 0.046 Uiso 1 1 calc R U . . .
C10 C 0.7091(6) 0.7132(5) 0.51661(18) 0.0340(15) Uani 1 1 d . . . . .
H10A H 0.755551 0.658479 0.526462 0.041 Uiso 1 1 calc R U . . .
H10B H 0.649427 0.687924 0.497343 0.041 Uiso 1 1 calc R U . . .
C11 C 0.5791(5) 0.6930(4) 0.58129(17) 0.0290(14) Uani 1 1 d . . . . .
C12 C 0.5954(9) 0.5957(6) 0.5817(3) 0.089(4) Uani 1 1 d . . . . .
H12 H 0.657171 0.569689 0.566138 0.106 Uiso 1 1 calc R U . . .
C13 C 0.5245(10) 0.5338(6) 0.6041(3) 0.089(4) Uani 1 1 d . . . . .
C14 C 0.4346(6) 0.5662(6) 0.62516(19) 0.0428(18) Uani 1 1 d . . . . .
C15 C 0.4183(10) 0.6599(8) 0.6253(4) 0.114(5) Uani 1 1 d . . . . .
H15 H 0.354889 0.684598 0.640333 0.137 Uiso 1 1 calc R U . . .
C16 C 0.4895(9) 0.7235(7) 0.6046(3) 0.098(4) Uani 1 1 d . . . . .
H16 H 0.475086 0.790274 0.606781 0.118 Uiso 1 1 calc R U . . .
C17 C 0.3421(6) 0.5059(5) 0.6872(2) 0.0358(15) Uani 1 1 d . . . . .
C18 C 0.2406(6) 0.4692(5) 0.7031(2) 0.0362(15) Uani 1 1 d . . . . .
H18 H 0.185214 0.442646 0.684427 0.043 Uiso 1 1 calc R U . . .
C19 C 0.2256(6) 0.4737(4) 0.7464(2) 0.0317(14) Uani 1 1 d . . . . .
H19 H 0.158803 0.451129 0.759917 0.038 Uiso 1 1 calc R U . . .
C20 C 0.3142(5) 0.5133(4) 0.77033(18) 0.0295(14) Uani 1 1 d . . . . .
C21 C 0.3853(5) 0.5498(5) 0.84069(18) 0.0333(15) Uani 1 1 d . . . . .
C22 C 0.4796(6) 0.4958(5) 0.8466(2) 0.0382(16) Uani 1 1 d . . . . .
H22 H 0.490298 0.439127 0.830009 0.046 Uiso 1 1 calc R U . . .
C23 C 0.5597(6) 0.5233(5) 0.87648(19) 0.0373(15) Uani 1 1 d . . . . .
H23 H 0.624756 0.484598 0.880251 0.045 Uiso 1 1 calc R U . . .
C24 C 0.5479(5) 0.6064(4) 0.90144(17) 0.0271(13) Uani 1 1 d . . . . .
C25 C 0.4524(6) 0.6602(4) 0.89452(19) 0.0322(14) Uani 1 1 d . . . . .
H25 H 0.441144 0.717017 0.910949 0.039 Uiso 1 1 calc R U . . .
C26 C 0.3722(6) 0.6334(5) 0.8640(2) 0.0358(15) Uani 1 1 d . . . . .
C27 C 0.6393(5) 0.6395(4) 0.93325(17) 0.0290(14) Uani 1 1 d . . . . .
C28 C 0.7072(6) 0.5544(5) 0.9514(2) 0.0396(17) Uani 1 1 d . . . . .
H28A H 0.656357 0.510741 0.967382 0.047 Uiso 1 1 calc R U . . .
H28B H 0.741372 0.518051 0.927181 0.047 Uiso 1 1 calc R U . . .
C29 C 0.8001(6) 0.5907(5) 0.98185(19) 0.0388(16) Uani 1 1 d . . . . .
H29 H 0.843102 0.534617 0.993413 0.047 Uiso 1 1 calc R U . . .
C30 C 0.8800(5) 0.6551(5) 0.95624(18) 0.0323(15) Uani 1 1 d . . . . .
H30A H 0.913232 0.618393 0.931952 0.039 Uiso 1 1 calc R U . . .
H30B H 0.941964 0.676882 0.975272 0.039 Uiso 1 1 calc R U . . .
C31 C 0.8159(5) 0.7430(4) 0.93830(17) 0.0256(13) Uani 1 1 d . . . . .
C32 C 0.7202(5) 0.7065(4) 0.90879(16) 0.0226(12) Uani 1 1 d . . . . .
H32A H 0.677548 0.762035 0.897372 0.027 Uiso 1 1 calc R U . . .
H32B H 0.753022 0.671781 0.883850 0.027 Uiso 1 1 calc R U . . .
C33 C 0.7479(6) 0.6458(6) 1.01969(19) 0.047(2) Uani 1 1 d . . . . .
H33A H 0.697304 0.603235 1.036366 0.057 Uiso 1 1 calc R U . . .
H33B H 0.807820 0.669098 1.039348 0.057 Uiso 1 1 calc R U . . .
C34 C 0.5885(6) 0.6957(5) 0.97177(18) 0.0373(16) Uani 1 1 d . . . . .
H34A H 0.546048 0.751822 0.960838 0.045 Uiso 1 1 calc R U . . .
H34B H 0.535616 0.654121 0.987928 0.045 Uiso 1 1 calc R U . . .
C35 C 0.6826(6) 0.7293(6) 1.00189(19) 0.0416(18) Uani 1 1 d . . . . .
H35 H 0.648390 0.765418 1.026590 0.050 Uiso 1 1 calc R U . . .
C36 C 0.7616(5) 0.7978(5) 0.97649(17) 0.0328(15) Uani 1 1 d . . . . .
H36A H 0.718046 0.853013 0.965345 0.039 Uiso 1 1 calc R U . . .
H36B H 0.821017 0.822471 0.995997 0.039 Uiso 1 1 calc R U . . .
C37 C 0.8969(5) 0.8056(4) 0.91234(16) 0.0234(12) Uani 1 1 d . . . . .
C38 C 0.9444(5) 0.7708(4) 0.87373(17) 0.0288(13) Uani 1 1 d . . . . .
H38 H 0.921435 0.710018 0.863050 0.035 Uiso 1 1 calc R U . . .
C39 C 1.0239(5) 0.8228(4) 0.85087(18) 0.0299(14) Uani 1 1 d . . . . .
H39 H 1.054332 0.797591 0.824783 0.036 Uiso 1 1 calc R U . . .
C40 C 1.0587(5) 0.9100(4) 0.86565(17) 0.0262(13) Uani 1 1 d . . . . .
C41 C 1.0123(5) 0.9455(4) 0.90338(18) 0.0273(13) Uani 1 1 d . . . . .
C42 C 0.9315(5) 0.8942(4) 0.92590(17) 0.0273(13) Uani 1 1 d . . . . .
H42 H 0.899412 0.921051 0.951327 0.033 Uiso 1 1 calc R U . . .
C43 C 1.1537(5) 0.9691(4) 0.80262(19) 0.0299(13) Uani 1 1 d . . . . .
C44 C 1.2583(6) 0.9993(5) 0.7862(2) 0.0351(15) Uani 1 1 d . . . . .
H44 H 1.320726 1.011124 0.804649 0.042 Uiso 1 1 calc R U . . .
C45 C 1.2652(6) 1.0105(5) 0.7428(2) 0.0363(15) Uani 1 1 d . . . . .
H45 H 1.332717 1.030831 0.729153 0.044 Uiso 1 1 calc R U . . .
C46 C 1.1680(6) 0.9905(4) 0.71921(19) 0.0315(14) Uani 1 1 d . . . . .
C47 C 1.0847(6) 0.9704(5) 0.64948(19) 0.0356(16) Uani 1 1 d . . . . .
C48 C 0.9836(6) 1.0172(5) 0.6472(2) 0.0382(16) Uani 1 1 d . . . . .
H48 H 0.970048 1.071337 0.665095 0.046 Uiso 1 1 calc R U . . .
C49 C 0.9016(6) 0.9864(5) 0.61902(18) 0.0379(16) Uani 1 1 d . . . . .
H49 H 0.831581 1.019240 0.617836 0.045 Uiso 1 1 calc R U . . .
C50 C 0.9200(6) 0.9070(5) 0.59200(18) 0.0317(14) Uani 1 1 d . . . . .
C51 C 1.0214(6) 0.8610(5) 0.5950(2) 0.0361(15) Uani 1 1 d . . . . .
H51 H 1.035474 0.806761 0.577221 0.043 Uiso 1 1 calc R U . . .
C52 C 1.1035(6) 0.8918(5) 0.6233(2) 0.0363(15) Uani 1 1 d . . . . .
C53 C 1.0277(7) 0.7394(6) 0.7153(2) 0.053(2) Uani 1 1 d . . . . .
H53 H 1.020804 0.807501 0.705483 0.064 Uiso 1 1 calc R U . . .
C54 C 0.5568(6) 0.7339(5) 0.7487(2) 0.0484(18) Uani 1 1 d . . . . .
H54 H 0.527806 0.667294 0.744357 0.058 Uiso 1 1 calc R U . . .
N1 N 0.4224(5) 0.5418(4) 0.71066(15) 0.0359(13) Uani 1 1 d . . . . .
N2 N 0.4071(4) 0.5456(4) 0.75456(15) 0.0312(12) Uani 1 1 d . . . . .
N3 N 1.0644(5) 0.9503(4) 0.77943(14) 0.0293(11) Uani 1 1 d . . . . .
N4 N 1.0721(4) 0.9603(3) 0.73540(15) 0.0285(11) Uani 1 1 d . . . . .
O1 O 0.3573(4) 0.5024(4) 0.64293(14) 0.0558(15) Uani 1 1 d . . . . .
O2 O 0.2972(4) 0.5184(4) 0.81416(14) 0.0417(12) Uani 1 1 d . . . . .
O3 O 1.1466(4) 0.9613(3) 0.84661(12) 0.0355(10) Uani 1 1 d . . . . .
O4 O 1.1738(4) 1.0043(4) 0.67489(14) 0.0423(12) Uani 1 1 d . . . . .
Cl2 Cl 0.25394(17) 0.70495(15) 0.85639(7) 0.0618(6) Uani 1 1 d . . . . .
Cl3 Cl 1.05866(16) 1.05605(11) 0.92329(5) 0.0412(4) Uani 1 1 d . . . . .
Cl4 Cl 1.22938(17) 0.82983(15) 0.62606(7) 0.0574(5) Uani 1 1 d . . . . .
Cl5 Cl 1.1611(2) 0.72482(15) 0.73901(7) 0.0649(6) Uani 1 1 d . . . . .
Cl6 Cl 1.0124(3) 0.66518(15) 0.66965(6) 0.0794(8) Uani 1 1 d . . . . .
Cl7 Cl 0.9212(2) 0.71745(17) 0.75307(8) 0.0722(6) Uani 1 1 d . . . . .
Cl8 Cl 0.6475(2) 0.76157(16) 0.70552(6) 0.0625(6) Uani 1 1 d . . . . .
Cl9 Cl 0.6293(2) 0.73772(15) 0.79821(6) 0.0608(6) Uani 1 1 d . . . . .
Cl10 Cl 0.4424(2) 0.81221(17) 0.74917(9) 0.0798(7) Uani 1 1 d . . . . .
Cl1A Cl 0.5856(3) 0.4124(2) 0.61947(11) 0.0521(11) Uani 0.568(5) 1 d . . P A 1
Cl1B Cl 0.4866(5) 0.4240(3) 0.57938(17) 0.070(2) Uani 0.432(5) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C50 1.536(9) . ?
C1 C2 1.542(9) . ?
C1 C7 1.547(8) . ?
C1 C6 1.551(8) . ?
C2 C3 1.530(9) . ?
C2 H2A 0.9900 . ?
C2 H2AB 0.9900 . ?
C3 C4 1.526(9) . ?
C3 C8 1.529(9) . ?
C3 H3 1.0000 . ?
C4 C5 1.539(8) . ?
C4 H4A 0.9900 . ?
C4 H4AB 0.9900 . ?
C5 C11 1.524(8) . ?
C5 C6 1.546(8) . ?
C5 C10 1.549(8) . ?
C6 H6A 0.9900 . ?
C6 H6AB 0.9900 . ?
C7 C9 1.537(9) . ?
C7 H7A 0.9900 . ?
C7 H7AB 0.9900 . ?
C8 C9 1.534(10) . ?
C8 H8A 0.9900 . ?
C8 H8AB 0.9900 . ?
C9 C10 1.520(9) . ?
C9 H9 1.0000 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.354(10) . ?
C11 C12 1.371(10) . ?
C12 C13 1.390(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.329(11) . ?
C13 Cl1B 1.770(9) . ?
C13 Cl1A 1.903(11) . ?
C14 C15 1.321(12) . ?
C14 O1 1.392(8) . ?
C15 C16 1.382(13) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 N1 1.298(8) . ?
C17 O1 1.381(7) . ?
C17 C18 1.399(9) . ?
C18 C19 1.351(8) . ?
C18 H18 0.9500 . ?
C19 C20 1.399(8) . ?
C19 H19 0.9500 . ?
C20 N2 1.288(8) . ?
C20 O2 1.370(7) . ?
C21 C22 1.363(10) . ?
C21 C26 1.379(9) . ?
C21 O2 1.400(7) . ?
C22 C23 1.380(9) . ?
C22 H22 0.9500 . ?
C23 C24 1.399(8) . ?
C23 H23 0.9500 . ?
C24 C25 1.377(9) . ?
C24 C27 1.535(8) . ?
C25 C26 1.391(8) . ?
C25 H25 0.9500 . ?
C26 Cl2 1.739(7) . ?
C27 C32 1.539(8) . ?
C27 C28 1.541(9) . ?
C27 C34 1.547(8) . ?
C28 C29 1.536(9) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.527(9) . ?
C29 C33 1.530(10) . ?
C29 H29 1.0000 . ?
C30 C31 1.546(8) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C37 1.527(8) . ?
C31 C32 1.543(7) . ?
C31 C36 1.546(7) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C35 1.504(11) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C34 C35 1.528(9) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.552(9) . ?
C35 H35 1.0000 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C42 1.368(8) . ?
C37 C38 1.405(7) . ?
C38 C39 1.384(8) . ?
C38 H38 0.9500 . ?
C39 C40 1.364(8) . ?
C39 H39 0.9500 . ?
C40 C41 1.380(8) . ?
C40 O3 1.395(7) . ?
C41 C42 1.385(8) . ?
C41 Cl3 1.749(6) . ?
C42 H42 0.9500 . ?
C43 N3 1.306(8) . ?
C43 O3 1.365(7) . ?
C43 C44 1.406(9) . ?
C44 C45 1.350(9) . ?
C44 H44 0.9500 . ?
C45 C46 1.394(9) . ?
C45 H45 0.9500 . ?
C46 N4 1.313(8) . ?
C46 O4 1.383(7) . ?
C47 C48 1.369(10) . ?
C47 C52 1.381(9) . ?
C47 O4 1.400(8) . ?
C48 C49 1.374(9) . ?
C48 H48 0.9500 . ?
C49 C50 1.404(9) . ?
C49 H49 0.9500 . ?
C50 C51 1.368(10) . ?
C51 C52 1.378(9) . ?
C51 H51 0.9500 . ?
C52 Cl4 1.729(7) . ?
C53 Cl7 1.748(8) . ?
C53 Cl6 1.757(7) . ?
C53 Cl5 1.758(8) . ?
C53 H53 1.0000 . ?
C54 Cl10 1.745(8) . ?
C54 Cl9 1.755(8) . ?
C54 Cl8 1.756(8) . ?
C54 H54 1.0000 . ?
N1 N2 1.368(7) . ?
N3 N4 1.369(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C50 C1 C2 111.9(5) . . ?
C50 C1 C7 111.3(5) . . ?
C2 C1 C7 107.8(5) . . ?
C50 C1 C6 109.5(4) . . ?
C2 C1 C6 108.5(5) . . ?
C7 C1 C6 107.7(5) . . ?
C3 C2 C1 110.8(5) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2AB 109.5 . . ?
C1 C2 H2AB 109.5 . . ?
H2A C2 H2AB 108.1 . . ?
C4 C3 C8 110.3(6) . . ?
C4 C3 C2 109.0(5) . . ?
C8 C3 C2 110.0(6) . . ?
C4 C3 H3 109.2 . . ?
C8 C3 H3 109.2 . . ?
C2 C3 H3 109.2 . . ?
C3 C4 C5 111.4(5) . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4AB 109.3 . . ?
C5 C4 H4AB 109.3 . . ?
H4A C4 H4AB 108.0 . . ?
C11 C5 C4 111.0(5) . . ?
C11 C5 C6 110.4(4) . . ?
C4 C5 C6 108.1(5) . . ?
C11 C5 C10 111.5(5) . . ?
C4 C5 C10 107.7(4) . . ?
C6 C5 C10 108.2(5) . . ?
C5 C6 C1 111.5(4) . . ?
C5 C6 H6A 109.3 . . ?
C1 C6 H6A 109.3 . . ?
C5 C6 H6AB 109.3 . . ?
C1 C6 H6AB 109.3 . . ?
H6A C6 H6AB 108.0 . . ?
C9 C7 C1 111.2(5) . . ?
C9 C7 H7A 109.4 . . ?
C1 C7 H7A 109.4 . . ?
C9 C7 H7AB 109.4 . . ?
C1 C7 H7AB 109.4 . . ?
H7A C7 H7AB 108.0 . . ?
C3 C8 C9 108.3(5) . . ?
C3 C8 H8A 110.0 . . ?
C9 C8 H8A 110.0 . . ?
C3 C8 H8AB 110.0 . . ?
C9 C8 H8AB 110.0 . . ?
H8A C8 H8AB 108.4 . . ?
C10 C9 C8 110.8(5) . . ?
C10 C9 C7 108.4(5) . . ?
C8 C9 C7 109.4(6) . . ?
C10 C9 H9 109.4 . . ?
C8 C9 H9 109.4 . . ?
C7 C9 H9 109.4 . . ?
C9 C10 C5 111.1(5) . . ?
C9 C10 H10A 109.4 . . ?
C5 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C5 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C16 C11 C12 114.6(7) . . ?
C16 C11 C5 122.0(6) . . ?
C12 C11 C5 123.4(6) . . ?
C11 C12 C13 122.3(7) . . ?
C11 C12 H12 118.8 . . ?
C13 C12 H12 118.8 . . ?
C14 C13 C12 121.2(8) . . ?
C14 C13 Cl1B 107.5(7) . . ?
C12 C13 Cl1B 118.5(6) . . ?
C14 C13 Cl1A 119.2(7) . . ?
C12 C13 Cl1A 116.5(8) . . ?
C15 C14 C13 117.1(7) . . ?
C15 C14 O1 122.3(8) . . ?
C13 C14 O1 120.4(7) . . ?
C14 C15 C16 122.9(8) . . ?
C14 C15 H15 118.5 . . ?
C16 C15 H15 118.5 . . ?
C11 C16 C15 121.7(8) . . ?
C11 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
N1 C17 O1 118.0(6) . . ?
N1 C17 C18 125.5(6) . . ?
O1 C17 C18 116.5(6) . . ?
C19 C18 C17 116.3(6) . . ?
C19 C18 H18 121.9 . . ?
C17 C18 H18 121.9 . . ?
C18 C19 C20 116.2(6) . . ?
C18 C19 H19 121.9 . . ?
C20 C19 H19 121.9 . . ?
N2 C20 O2 118.8(5) . . ?
N2 C20 C19 125.7(5) . . ?
O2 C20 C19 115.5(6) . . ?
C22 C21 C26 119.4(6) . . ?
C22 C21 O2 121.3(6) . . ?
C26 C21 O2 119.1(6) . . ?
C21 C22 C23 120.1(6) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C24 122.0(7) . . ?
C22 C23 H23 119.0 . . ?
C24 C23 H23 119.0 . . ?
C25 C24 C23 116.7(6) . . ?
C25 C24 C27 121.2(5) . . ?
C23 C24 C27 122.1(6) . . ?
C24 C25 C26 121.5(6) . . ?
C24 C25 H25 119.2 . . ?
C26 C25 H25 119.2 . . ?
C21 C26 C25 120.2(6) . . ?
C21 C26 Cl2 120.4(5) . . ?
C25 C26 Cl2 119.4(5) . . ?
C24 C27 C32 108.1(4) . . ?
C24 C27 C28 111.8(5) . . ?
C32 C27 C28 108.6(5) . . ?
C24 C27 C34 111.6(5) . . ?
C32 C27 C34 108.2(5) . . ?
C28 C27 C34 108.4(5) . . ?
C29 C28 C27 110.2(6) . . ?
C29 C28 H28A 109.6 . . ?
C27 C28 H28A 109.6 . . ?
C29 C28 H28B 109.6 . . ?
C27 C28 H28B 109.6 . . ?
H28A C28 H28B 108.1 . . ?
C30 C29 C33 110.6(6) . . ?
C30 C29 C28 108.9(5) . . ?
C33 C29 C28 110.0(6) . . ?
C30 C29 H29 109.1 . . ?
C33 C29 H29 109.1 . . ?
C28 C29 H29 109.1 . . ?
C29 C30 C31 110.2(5) . . ?
C29 C30 H30A 109.6 . . ?
C31 C30 H30A 109.6 . . ?
C29 C30 H30B 109.6 . . ?
C31 C30 H30B 109.6 . . ?
H30A C30 H30B 108.1 . . ?
C37 C31 C32 110.1(4) . . ?
C37 C31 C30 109.3(5) . . ?
C32 C31 C30 108.3(5) . . ?
C37 C31 C36 112.3(5) . . ?
C32 C31 C36 107.8(5) . . ?
C30 C31 C36 109.0(5) . . ?
C27 C32 C31 111.8(4) . . ?
C27 C32 H32A 109.3 . . ?
C31 C32 H32A 109.3 . . ?
C27 C32 H32B 109.3 . . ?
C31 C32 H32B 109.3 . . ?
H32A C32 H32B 107.9 . . ?
C35 C33 C29 108.7(5) . . ?
C35 C33 H33A 110.0 . . ?
C29 C33 H33A 110.0 . . ?
C35 C33 H33B 110.0 . . ?
C29 C33 H33B 110.0 . . ?
H33A C33 H33B 108.3 . . ?
C35 C34 C27 109.7(5) . . ?
C35 C34 H34A 109.7 . . ?
C27 C34 H34A 109.7 . . ?
C35 C34 H34B 109.7 . . ?
C27 C34 H34B 109.7 . . ?
H34A C34 H34B 108.2 . . ?
C33 C35 C34 111.3(6) . . ?
C33 C35 C36 110.4(6) . . ?
C34 C35 C36 108.9(5) . . ?
C33 C35 H35 108.7 . . ?
C34 C35 H35 108.7 . . ?
C36 C35 H35 108.7 . . ?
C31 C36 C35 109.5(5) . . ?
C31 C36 H36A 109.8 . . ?
C35 C36 H36A 109.8 . . ?
C31 C36 H36B 109.8 . . ?
C35 C36 H36B 109.8 . . ?
H36A C36 H36B 108.2 . . ?
C42 C37 C38 116.8(5) . . ?
C42 C37 C31 123.1(5) . . ?
C38 C37 C31 120.0(5) . . ?
C39 C38 C37 121.7(5) . . ?
C39 C38 H38 119.1 . . ?
C37 C38 H38 119.1 . . ?
C40 C39 C38 120.3(5) . . ?
C40 C39 H39 119.9 . . ?
C38 C39 H39 119.9 . . ?
C39 C40 C41 118.7(5) . . ?
C39 C40 O3 122.9(5) . . ?
C41 C40 O3 118.1(5) . . ?
C40 C41 C42 121.0(5) . . ?
C40 C41 Cl3 119.1(5) . . ?
C42 C41 Cl3 119.9(4) . . ?
C37 C42 C41 121.5(5) . . ?
C37 C42 H42 119.3 . . ?
C41 C42 H42 119.3 . . ?
N3 C43 O3 118.6(5) . . ?
N3 C43 C44 125.4(6) . . ?
O3 C43 C44 115.9(5) . . ?
C45 C44 C43 116.5(6) . . ?
C45 C44 H44 121.8 . . ?
C43 C44 H44 121.8 . . ?
C44 C45 C46 116.4(6) . . ?
C44 C45 H45 121.8 . . ?
C46 C45 H45 121.8 . . ?
N4 C46 O4 117.7(6) . . ?
N4 C46 C45 125.7(6) . . ?
O4 C46 C45 116.6(6) . . ?
C48 C47 C52 119.3(6) . . ?
C48 C47 O4 122.1(6) . . ?
C52 C47 O4 118.3(6) . . ?
C47 C48 C49 120.4(6) . . ?
C47 C48 H48 119.8 . . ?
C49 C48 H48 119.8 . . ?
C48 C49 C50 120.8(7) . . ?
C48 C49 H49 119.6 . . ?
C50 C49 H49 119.6 . . ?
C51 C50 C49 117.9(6) . . ?
C51 C50 C1 121.9(6) . . ?
C49 C50 C1 120.2(6) . . ?
C50 C51 C52 121.4(6) . . ?
C50 C51 H51 119.3 . . ?
C52 C51 H51 119.3 . . ?
C51 C52 C47 120.2(6) . . ?
C51 C52 Cl4 119.2(5) . . ?
C47 C52 Cl4 120.5(5) . . ?
Cl7 C53 Cl6 110.9(4) . . ?
Cl7 C53 Cl5 110.7(4) . . ?
Cl6 C53 Cl5 111.0(5) . . ?
Cl7 C53 H53 108.0 . . ?
Cl6 C53 H53 108.0 . . ?
Cl5 C53 H53 108.0 . . ?
Cl10 C54 Cl9 110.9(4) . . ?
Cl10 C54 Cl8 110.3(4) . . ?
Cl9 C54 Cl8 110.7(4) . . ?
Cl10 C54 H54 108.3 . . ?
Cl9 C54 H54 108.3 . . ?
Cl8 C54 H54 108.3 . . ?
C17 N1 N2 117.9(5) . . ?
C20 N2 N1 118.4(5) . . ?
C43 N3 N4 118.0(5) . . ?
C46 N4 N3 117.9(5) . . ?
C17 O1 C14 117.0(5) . . ?
C20 O2 C21 118.9(5) . . ?
C43 O3 C40 120.4(5) . . ?
C46 O4 C47 118.0(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C50 C1 C2 C3 -179.6(5) . . . . ?
C7 C1 C2 C3 57.7(7) . . . . ?
C6 C1 C2 C3 -58.7(6) . . . . ?
C1 C2 C3 C4 60.0(7) . . . . ?
C1 C2 C3 C8 -61.0(7) . . . . ?
C8 C3 C4 C5 60.4(7) . . . . ?
C2 C3 C4 C5 -60.4(7) . . . . ?
C3 C4 C5 C11 -179.9(5) . . . . ?
C3 C4 C5 C6 58.9(6) . . . . ?
C3 C4 C5 C10 -57.7(7) . . . . ?
C11 C5 C6 C1 -179.4(5) . . . . ?
C4 C5 C6 C1 -57.9(6) . . . . ?
C10 C5 C6 C1 58.4(6) . . . . ?
C50 C1 C6 C5 -179.5(5) . . . . ?
C2 C1 C6 C5 58.1(6) . . . . ?
C7 C1 C6 C5 -58.3(6) . . . . ?
C50 C1 C7 C9 179.2(5) . . . . ?
C2 C1 C7 C9 -57.7(7) . . . . ?
C6 C1 C7 C9 59.2(7) . . . . ?
C4 C3 C8 C9 -59.1(8) . . . . ?
C2 C3 C8 C9 61.1(7) . . . . ?
C3 C8 C9 C10 59.1(7) . . . . ?
C3 C8 C9 C7 -60.4(7) . . . . ?
C1 C7 C9 C10 -60.8(7) . . . . ?
C1 C7 C9 C8 60.2(7) . . . . ?
C8 C9 C10 C5 -59.6(6) . . . . ?
C7 C9 C10 C5 60.6(7) . . . . ?
C11 C5 C10 C9 179.1(5) . . . . ?
C4 C5 C10 C9 57.2(7) . . . . ?
C6 C5 C10 C9 -59.4(6) . . . . ?
C4 C5 C11 C16 -32.0(9) . . . . ?
C6 C5 C11 C16 87.8(9) . . . . ?
C10 C5 C11 C16 -152.0(8) . . . . ?
C4 C5 C11 C12 147.3(8) . . . . ?
C6 C5 C11 C12 -93.0(9) . . . . ?
C10 C5 C11 C12 27.3(9) . . . . ?
C16 C11 C12 C13 0.4(16) . . . . ?
C5 C11 C12 C13 -178.9(9) . . . . ?
C11 C12 C13 C14 2.4(19) . . . . ?
C11 C12 C13 Cl1B 139.1(9) . . . . ?
C11 C12 C13 Cl1A -157.5(8) . . . . ?
C12 C13 C14 C15 -2.7(16) . . . . ?
Cl1B C13 C14 C15 -143.6(9) . . . . ?
Cl1A C13 C14 C15 156.6(9) . . . . ?
C12 C13 C14 O1 172.2(9) . . . . ?
Cl1B C13 C14 O1 31.3(11) . . . . ?
Cl1A C13 C14 O1 -28.5(12) . . . . ?
C13 C14 C15 C16 0.5(19) . . . . ?
O1 C14 C15 C16 -174.3(10) . . . . ?
C12 C11 C16 C15 -2.7(16) . . . . ?
C5 C11 C16 C15 176.6(10) . . . . ?
C14 C15 C16 C11 2(2) . . . . ?
N1 C17 C18 C19 1.2(11) . . . . ?
O1 C17 C18 C19 -179.4(6) . . . . ?
C17 C18 C19 C20 -0.8(10) . . . . ?
C18 C19 C20 N2 0.2(10) . . . . ?
C18 C19 C20 O2 179.2(6) . . . . ?
C26 C21 C22 C23 1.8(10) . . . . ?
O2 C21 C22 C23 -172.9(6) . . . . ?
C21 C22 C23 C24 -0.3(10) . . . . ?
C22 C23 C24 C25 -0.4(9) . . . . ?
C22 C23 C24 C27 -177.2(6) . . . . ?
C23 C24 C25 C26 -0.4(9) . . . . ?
C27 C24 C25 C26 176.4(6) . . . . ?
C22 C21 C26 C25 -2.6(9) . . . . ?
O2 C21 C26 C25 172.2(6) . . . . ?
C22 C21 C26 Cl2 178.7(5) . . . . ?
O2 C21 C26 Cl2 -6.5(8) . . . . ?
C24 C25 C26 C21 1.9(10) . . . . ?
C24 C25 C26 Cl2 -179.4(5) . . . . ?
C25 C24 C27 C32 -86.2(7) . . . . ?
C23 C24 C27 C32 90.4(7) . . . . ?
C25 C24 C27 C28 154.3(6) . . . . ?
C23 C24 C27 C28 -29.0(8) . . . . ?
C25 C24 C27 C34 32.7(8) . . . . ?
C23 C24 C27 C34 -150.7(6) . . . . ?
C24 C27 C28 C29 178.1(5) . . . . ?
C32 C27 C28 C29 58.9(6) . . . . ?
C34 C27 C28 C29 -58.4(7) . . . . ?
C27 C28 C29 C30 -61.2(7) . . . . ?
C27 C28 C29 C33 60.0(7) . . . . ?
C33 C29 C30 C31 -59.4(7) . . . . ?
C28 C29 C30 C31 61.5(7) . . . . ?
C29 C30 C31 C37 -179.3(5) . . . . ?
C29 C30 C31 C32 -59.3(6) . . . . ?
C29 C30 C31 C36 57.6(6) . . . . ?
C24 C27 C32 C31 -179.5(5) . . . . ?
C28 C27 C32 C31 -58.1(6) . . . . ?
C34 C27 C32 C31 59.4(6) . . . . ?
C37 C31 C32 C27 177.6(5) . . . . ?
C30 C31 C32 C27 58.1(6) . . . . ?
C36 C31 C32 C27 -59.6(6) . . . . ?
C30 C29 C33 C35 60.5(7) . . . . ?
C28 C29 C33 C35 -59.7(7) . . . . ?
C24 C27 C34 C35 -178.6(5) . . . . ?
C32 C27 C34 C35 -59.7(7) . . . . ?
C28 C27 C34 C35 57.9(7) . . . . ?
C29 C33 C35 C34 60.3(7) . . . . ?
C29 C33 C35 C36 -60.8(7) . . . . ?
C27 C34 C35 C33 -60.2(7) . . . . ?
C27 C34 C35 C36 61.7(7) . . . . ?
C37 C31 C36 C35 -178.8(5) . . . . ?
C32 C31 C36 C35 59.8(6) . . . . ?
C30 C31 C36 C35 -57.5(6) . . . . ?
C33 C35 C36 C31 60.4(7) . . . . ?
C34 C35 C36 C31 -62.0(7) . . . . ?
C32 C31 C37 C42 130.6(6) . . . . ?
C30 C31 C37 C42 -110.6(6) . . . . ?
C36 C31 C37 C42 10.5(8) . . . . ?
C32 C31 C37 C38 -52.9(7) . . . . ?
C30 C31 C37 C38 65.9(6) . . . . ?
C36 C31 C37 C38 -173.1(5) . . . . ?
C42 C37 C38 C39 1.1(9) . . . . ?
C31 C37 C38 C39 -175.6(6) . . . . ?
C37 C38 C39 C40 0.3(9) . . . . ?
C38 C39 C40 C41 -0.7(9) . . . . ?
C38 C39 C40 O3 173.2(6) . . . . ?
C39 C40 C41 C42 -0.3(9) . . . . ?
O3 C40 C41 C42 -174.5(5) . . . . ?
C39 C40 C41 Cl3 178.6(5) . . . . ?
O3 C40 C41 Cl3 4.4(7) . . . . ?
C38 C37 C42 C41 -2.1(9) . . . . ?
C31 C37 C42 C41 174.4(5) . . . . ?
C40 C41 C42 C37 1.8(9) . . . . ?
Cl3 C41 C42 C37 -177.1(5) . . . . ?
N3 C43 C44 C45 0.8(10) . . . . ?
O3 C43 C44 C45 -177.8(6) . . . . ?
C43 C44 C45 C46 -0.2(9) . . . . ?
C44 C45 C46 N4 -1.4(10) . . . . ?
C44 C45 C46 O4 178.3(6) . . . . ?
C52 C47 C48 C49 0.0(9) . . . . ?
O4 C47 C48 C49 174.4(6) . . . . ?
C47 C48 C49 C50 -0.4(10) . . . . ?
C48 C49 C50 C51 0.7(9) . . . . ?
C48 C49 C50 C1 178.6(6) . . . . ?
C2 C1 C50 C51 -149.1(6) . . . . ?
C7 C1 C50 C51 -28.4(8) . . . . ?
C6 C1 C50 C51 90.6(7) . . . . ?
C2 C1 C50 C49 33.2(7) . . . . ?
C7 C1 C50 C49 153.9(6) . . . . ?
C6 C1 C50 C49 -87.1(7) . . . . ?
C49 C50 C51 C52 -0.6(9) . . . . ?
C1 C50 C51 C52 -178.4(6) . . . . ?
C50 C51 C52 C47 0.1(10) . . . . ?
C50 C51 C52 Cl4 179.2(5) . . . . ?
C48 C47 C52 C51 0.2(9) . . . . ?
O4 C47 C52 C51 -174.4(6) . . . . ?
C48 C47 C52 Cl4 -178.9(5) . . . . ?
O4 C47 C52 Cl4 6.5(8) . . . . ?
O1 C17 N1 N2 179.8(6) . . . . ?
C18 C17 N1 N2 -0.9(10) . . . . ?
O2 C20 N2 N1 -178.8(6) . . . . ?
C19 C20 N2 N1 0.1(10) . . . . ?
C17 N1 N2 C20 0.2(9) . . . . ?
O3 C43 N3 N4 178.7(5) . . . . ?
C44 C43 N3 N4 0.2(9) . . . . ?
O4 C46 N4 N3 -177.3(5) . . . . ?
C45 C46 N4 N3 2.4(9) . . . . ?
C43 N3 N4 C46 -1.7(8) . . . . ?
N1 C17 O1 C14 -22.8(10) . . . . ?
C18 C17 O1 C14 157.9(6) . . . . ?
C15 C14 O1 C17 -66.4(11) . . . . ?
C13 C14 O1 C17 118.9(9) . . . . ?
N2 C20 O2 C21 -6.1(9) . . . . ?
C19 C20 O2 C21 174.8(6) . . . . ?
C22 C21 O2 C20 -68.8(8) . . . . ?
C26 C21 O2 C20 116.5(6) . . . . ?
N3 C43 O3 C40 17.5(8) . . . . ?
C44 C43 O3 C40 -163.8(5) . . . . ?
C39 C40 O3 C43 44.3(8) . . . . ?
C41 C40 O3 C43 -141.7(6) . . . . ?
N4 C46 O4 C47 -10.5(9) . . . . ?
C45 C46 O4 C47 169.8(6) . . . . ?
C48 C47 O4 C46 76.5(8) . . . . ?
C52 C47 O4 C46 -109.1(7) . . . . ?

_refine_diff_density_max         0.498
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.076

